Heteroatom-Centred Radicals for the Synthesis of Heterocyclic Compounds

  • Fabrice Dénès
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 54)


An overview of the synthetic methods allowing the preparation of heterocyclic structures based upon the use of heteroatom-centred radicals (R–X•) is presented here. The discussion will be limited to specific examples for which the heteroatom (X = SiR2, GeR2, SnR2, PR, NR, O, S, SO2, Se) is included in the heterocyclic structure itself during the cyclisation process leading to its formation. These include the cyclisation of heteroatom-centred radicals onto unsaturated partners such as alkenes, alkynes, arenes, ketones or nitriles and the formation of the heterocycle via a sequence involving remote functionalisation reactions leading to halogenated intermediates, followed by ionic cyclisation (e.g. Hofmann–Löffler–Freytag reaction), as well as cascade reactions terminating with an intramolecular homolytic substitution (SHi) at the heteroatom in the final step.


Alkoxy radicals Germyl radicals Heteroatom-centred radicals Intramolecular homolytic substitution (SHi) Intramolecular hydrogen atom transfer (1,n-HAT) Nitrogen-centred radicals Phosphorus-centred radicals Radical cyclisation Selenyl radicals Silyl radicals Sulphonyl radicals Thiol–ene Thiol–yne Thiyl radicals 


  1. 1.
    Landais Y (2013) In: Bellus D, Ley S, Noyori R, Trost B (eds) Science of synthesis. G. Thieme, vol 26Google Scholar
  2. 2.
    Roberts BP (1999) Chem Soc Rev 28:25CrossRefGoogle Scholar
  3. 3.
    Ballestri M, Chatgilialoglu C, Clark KB, Griller D, Giese B, Kopping B (1991) J Org Chem 56:678CrossRefGoogle Scholar
  4. 4.
    Chatgilialoglu C (1992) Acc Chem Res 25:188CrossRefGoogle Scholar
  5. 5.
    Kopping B, Chatgilialoglu C, Zehnder M, Giese B (1992) J Org Chem 57:3994CrossRefGoogle Scholar
  6. 6.
    Lusztyk J, Maillard B, Ingold KU (1986) J Org Chem 51:2457CrossRefGoogle Scholar
  7. 7.
    Lesage M, Martinho Simões JA, Griller D (1990) J Org Chem 55:5413CrossRefGoogle Scholar
  8. 8.
    Ballestri M, Chatgilialoglu C, Guerra M, Guerrini A, Lucarini M, Seconi G (1993) J Chem Soc Perkin Trans 2:421CrossRefGoogle Scholar
  9. 9.
    Newcomb M (1993) Tetrahedron 49:1151CrossRefGoogle Scholar
  10. 10.
    Chatgilialoglu C (1995) Chem Rev 95:1229CrossRefGoogle Scholar
  11. 11.
    Cai Y, Roberts BP (2002) J Chem Soc Perkin Trans 2:1858CrossRefGoogle Scholar
  12. 12.
    Roberts BP, Steel AJ (1994) J Chem Soc Perkin Trans 2:2155CrossRefGoogle Scholar
  13. 13.
    Roberts BP (1996) J Chem Soc Perkin Trans 2:2719CrossRefGoogle Scholar
  14. 14.
    Zavitsas AA, Chatgilialoglu C (1995) J Am Chem Soc 117:10645CrossRefGoogle Scholar
  15. 15.
    Chatgilialoglu C, Ingold KU, Scaiano JC (1983) J Am Chem Soc 105:3292CrossRefGoogle Scholar
  16. 16.
    Bennett SW, Eaborn C, Jackson RA, Pearce R (1968) J Organomet Chem 15:P17CrossRefGoogle Scholar
  17. 17.
    Sakurai H (1973) In: Kochi J (ed) Free radicals, vol 2. Wiley, New YorkGoogle Scholar
  18. 18.
    Chatgilialoglu C, Woynar H, Ingold KU, Davies AG (1983) J Chem Soc Perkin Trans 2:555CrossRefGoogle Scholar
  19. 19.
    Barton TJ, Revis A (1984) J Am Chem Soc 106:3802CrossRefGoogle Scholar
  20. 20.
    Beckwith ALJ, Schiesser CH (1985) Tetrahedron 41:3925CrossRefGoogle Scholar
  21. 21.
    Spellmeyer DC, Houk KN (1987) J Org Chem 52:959CrossRefGoogle Scholar
  22. 22.
    Sarasa JP, Igual J, Poblet JM (1986) J Chem Soc Perkin Trans 2:861CrossRefGoogle Scholar
  23. 23.
    Dang H-S, Roberts BP (1995) Tetrahedron Lett 36:2875CrossRefGoogle Scholar
  24. 24.
    Haque MB, Roberts BP (1996) Tetrahedron Lett 37:9123CrossRefGoogle Scholar
  25. 25.
    Ishibashi H, Sato T, Ikeda M (2002) Synthesis:695Google Scholar
  26. 26.
    Cai Y, Roberts BP (1998) J Chem Soc Perkin Trans 1:467CrossRefGoogle Scholar
  27. 27.
    Clive DLJ, Cantin M (1995) J Chem Soc Chem Commun:319Google Scholar
  28. 28.
    Clive DLJ, Yang W (1996) Chem Commun:1605Google Scholar
  29. 29.
    Sannigrahi M, Mayhew DL, Clive DLJ (1999) J Org Chem 64:2776PubMedCrossRefGoogle Scholar
  30. 30.
    Clive DLJ, Yang W, MacDonald AC, Wang Z, Cantin M (2001) J Org Chem 66:1966PubMedCrossRefGoogle Scholar
  31. 31.
    Clive DLJ, Ardelean E-S (2001) J Org Chem 66:4841PubMedCrossRefGoogle Scholar
  32. 32.
    Martinez-Grau A, Curran DP (1995) J Org Chem 60:8332CrossRefGoogle Scholar
  33. 33.
    Martinez-Grau A, Curran DP (1997) Tetrahedron 53:5679CrossRefGoogle Scholar
  34. 34.
    Schiesser CH, Matsubara H, Ritsner I, Wille U (2006) Chem Commun:1067Google Scholar
  35. 35.
    Schiesser CH, Wille U, Matsubara H, Ryu I (2007) Acc Chem Res 40:303PubMedCrossRefGoogle Scholar
  36. 36.
    Wille U, Tan JCS, Mucke E-K (2008) J Org Chem 73:5821PubMedCrossRefGoogle Scholar
  37. 37.
    Amrein S, Studer A (2002) Chem Commun:1592Google Scholar
  38. 38.
    Leifert D, Studer A (2015) Org Lett 17:386PubMedCrossRefGoogle Scholar
  39. 39.
    Kulicke K, Chatgilialoglu CS, Kopping B, Iese B (1992) Helv Chim Acta 75:935CrossRefGoogle Scholar
  40. 40.
    Miura K, Oshima K, Utimoto K (1992) Chem Lett 21:2477CrossRefGoogle Scholar
  41. 41.
    Miura K, Oshima K, Utimoto K (1993) Bull Chem Soc Jpn 66:2348CrossRefGoogle Scholar
  42. 42.
    Ryu I, Kurihara A, Muraoka H, Tsunoi S, Kambe N, Sonoda N (1994) J Org Chem 59:7570CrossRefGoogle Scholar
  43. 43.
    Matsubara H, Schiesser CH (2003) J Org Chem 68:9299PubMedCrossRefGoogle Scholar
  44. 44.
    Rouquet G, Robert F, Méreau R, Castet F, Renaud P, Landais Y (2012) Chem A Eur J 18:940CrossRefGoogle Scholar
  45. 45.
    Beckwith ALJ, Pigou PE (1986) Aust J Chem 39:1151CrossRefGoogle Scholar
  46. 46.
    Beckwith ALJ, Roberts DH, Schiesser CH, Wallner A (1985) Tetrahedron Lett 26:3349CrossRefGoogle Scholar
  47. 47.
    Pike P, Hershberger S, Hershberger J (1988) Tetrahedron 44:6295CrossRefGoogle Scholar
  48. 48.
    Russell Bowman W, Krintel SL, Schilling MB (2004) Org Biomol Chem 2:585PubMedCrossRefGoogle Scholar
  49. 49.
    Mochida K, Asami K (1982) J Organomet Chem 232:13CrossRefGoogle Scholar
  50. 50.
    Murai M, Takeshima H, Morita H, Kuninobu Y, Takai K (2015) J Org Chem 80:5407PubMedCrossRefGoogle Scholar
  51. 51.
    Allard N, Aïch RB, Gendron D, Boudreault P-LT, Tessier C, Alem S, Tse S-C, Tao Y, Leclerc M (2010) Macromolecules 43:2328CrossRefGoogle Scholar
  52. 52.
    Kuivila HG, Sommer R (1967) J Am Chem Soc 89:5616CrossRefGoogle Scholar
  53. 53.
    Krech F, Issleib K (1988) Z Anorg Allg Chem 557:143CrossRefGoogle Scholar
  54. 54.
    Connil M-F, Jousseaume B, Pereyre M (1996) Organometallics 15:4469CrossRefGoogle Scholar
  55. 55.
    Hays DS, Fu GC (1995) J Am Chem Soc 117:7283CrossRefGoogle Scholar
  56. 56.
    Kamimura A, Ishikawa S, Noguchi F, Moriyama T, So M, Murafuji T, Uno H (2012) Chem Commun 48:6592CrossRefGoogle Scholar
  57. 57.
    Kamimura A, Yoshinaga T, Noguchi F, Miyazaki K, Uno H (2015) Org Chem Front 2:713CrossRefGoogle Scholar
  58. 58.
    Hioe J, Sakic D, Vrcek V, Zipse H (2015) Org Biomol Chem 13:157PubMedCrossRefGoogle Scholar
  59. 59.
    Fallis AG, Brinza IM (1997) Tetrahedron 53:17543CrossRefGoogle Scholar
  60. 60.
    Kärkäs MD (2017) ACS Catal 7:4999CrossRefGoogle Scholar
  61. 61.
    Zard SZ (2008) Chem Soc Rev 37:1603CrossRefPubMedGoogle Scholar
  62. 62.
    Xiong T, Zhang Q (2016) Chem Soc Rev 45:3069PubMedPubMedCentralCrossRefGoogle Scholar
  63. 63.
    Chen J-R, Hu X-Q, Lu L-Q, Xiao W-J (2016) Chem Soc Rev 45:2044PubMedCrossRefGoogle Scholar
  64. 64.
    Newcomb M, Burchill MT, Deeb TM (1988) J Am Chem Soc 110:6528CrossRefGoogle Scholar
  65. 65.
    Musacchio AJ, Lainhart BC, Zhang X, Naguib SG, Sherwood TC, Knowles RR (2017) Science 355:727PubMedPubMedCentralCrossRefGoogle Scholar
  66. 66.
    Esker JL, Newcomb M (1993) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 58. Academic Press, New York, p 1Google Scholar
  67. 67.
    Maxwell BJ, Smith BJ, Tsanaktsidis J (2000) J Chem Soc Perkin Trans 2:425CrossRefGoogle Scholar
  68. 68.
    Newcomb M, Horner JH, Shahin H (1993) Tetrahedron Lett 34:5523CrossRefGoogle Scholar
  69. 69.
    Wagner BD, Ruel G, Lusztyk J (1996) J Am Chem Soc 118:13CrossRefGoogle Scholar
  70. 70.
    Newcomb M, Deeb TM (1987) J Am Chem Soc 109:3163CrossRefGoogle Scholar
  71. 71.
    Ha C, Musa OM, Martinez FN, Newcomb M (1997) J Org Chem 62:2704PubMedCrossRefGoogle Scholar
  72. 72.
    Maity S, Zheng N (2012) Angew Chem Int Ed 51:9562CrossRefGoogle Scholar
  73. 73.
    Li Y, Wang R, Wang T, Cheng X-F, Zhou X, Fei F, Wang X-S (2017) Angew Chem Int Ed 56:15436CrossRefGoogle Scholar
  74. 74.
    Musacchio AJ, Nguyen LQ, Beard GH, Knowles RR (2014) J Am Chem Soc 136:12217PubMedPubMedCentralCrossRefGoogle Scholar
  75. 75.
    Hu X-Q, Chen J-R, Wei Q, Liu F-L, Deng Q-H, Beauchemin AM, Xiao W-J (2014) Angew Chem Int Ed 53:12163CrossRefGoogle Scholar
  76. 76.
    Hu X-Q, Chen J, Chen J-R, Yan D-M, Xiao W-J (2016) Chem A Eur J 22:14141CrossRefGoogle Scholar
  77. 77.
    Hu X-Q, Qi X, Chen J-R, Zhao Q-Q, Wei Q, Lan Y, Xiao W-J (2016) Nat Commun 7:11188PubMedPubMedCentralCrossRefGoogle Scholar
  78. 78.
    Zhao Q-Q, Chen J, Yan D-M, Chen J-R, Xiao W-J (2017) Org Lett 19:3620PubMedCrossRefGoogle Scholar
  79. 79.
    Zhao Q-Q, Hu X-Q, Yang M-N, Chen J-R, Xiao W-J (2016) Chem Commun 52:12749Google Scholar
  80. 80.
    Brachet E, Marzo L, Selkti M, Konig B, Belmont P (2016) Chem Sci 7:5002CrossRefPubMedPubMedCentralGoogle Scholar
  81. 81.
    Newcomb M, Deeb TM, Marquardt DJ (1990) Tetrahedron 47:2317CrossRefGoogle Scholar
  82. 82.
    Balla RJ, Weiner BR, Nelson HH (1987) J Am Chem Soc 109:4804CrossRefGoogle Scholar
  83. 83.
    Bowman WR, Clark DN, Marmon RJ (1991) Tetrahedron Lett 32:6441CrossRefGoogle Scholar
  84. 84.
    Bowman RW, Clark DN, Marmon RJ (1992) Tetrahedron Lett 33:4993CrossRefGoogle Scholar
  85. 85.
    Bowman WR, Clark DN, Marmon RJ (1994) Tetrahedron 50:1275CrossRefGoogle Scholar
  86. 86.
    Bowman RW (1994) Tetrahedron 50:1295CrossRefGoogle Scholar
  87. 87.
    Bowman WR, Broadhurst MJ, Coghlan DR, Lewis KA (1997) Tetrahedron Lett 38:6301CrossRefGoogle Scholar
  88. 88.
    Liu F, Liu K, Yuang X, Li C (2007) J Org Chem 72:10231PubMedCrossRefGoogle Scholar
  89. 89.
    Zhai H, Wickenden JG, Sammis GM (2010) Synlett:3035Google Scholar
  90. 90.
    Zhai H, Zlotorzynska M, Sammis G (2009) Chem Commun:5716Google Scholar
  91. 91.
    Zlotorzynska M, Zhai H, Sammis GM (2010) J Org Chem 75:864PubMedCrossRefGoogle Scholar
  92. 92.
    Minisci F, Galli R (1966) Tetrahedron Lett 7:2531CrossRefGoogle Scholar
  93. 93.
    Stella L (1983) Angew Chem Int Ed 22:337CrossRefGoogle Scholar
  94. 94.
    Boate D, Fontaine C, Guittet E, Stella L (1993) Tetrahedron 49:8397CrossRefGoogle Scholar
  95. 95.
    Sjoholm A, Hemmerling M, Pradeille N, Somfai P (2001) J Chem Soc Perkin Trans 1:891CrossRefGoogle Scholar
  96. 96.
    Senboku H, Kajizuka Y, Hasegawa H, Fujita H, Suginome H, Orito K, Tokuda M (1999) Tetrahedron 55:6465CrossRefGoogle Scholar
  97. 97.
    White LV, Schwartz BD, Banwell MG, Willis AC (2011) J Org Chem 76:6250PubMedCrossRefGoogle Scholar
  98. 98.
    Ibrahim AA, Golonka AN, Lopez AM, Stockdill JL (2014) Org Lett 16:1072PubMedPubMedCentralCrossRefGoogle Scholar
  99. 99.
    Stockdill JL, Lopez AM, Ibrahim AA (2015) Tetrahedron Lett 56:3503PubMedPubMedCentralCrossRefGoogle Scholar
  100. 100.
    Corey EJ, Chen CP, Reichard GA (1989) Tetrahedron Lett 30:5547CrossRefGoogle Scholar
  101. 101.
    Lu H, Chen Q, Li C (2007) J Org Chem 72:2564PubMedCrossRefGoogle Scholar
  102. 102.
    Sherman ES, Chemler SR, Tan TB, Gerlits O (2004) Org Lett 6:1573CrossRefPubMedGoogle Scholar
  103. 103.
    Sherman ES, Fuller PH, Kasi D, Chemler SR (2007) J Org Chem 72:3896PubMedPubMedCentralCrossRefGoogle Scholar
  104. 104.
    Kim S, Joe GH, Do JY (1993) J Am Chem Soc 115:3328CrossRefGoogle Scholar
  105. 105.
    Kim S, Yoon KS, Kim SS, Seo HS (1995) Tetrahedron 51:8437CrossRefGoogle Scholar
  106. 106.
    Benati L, Bencivenni G, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Zanardi G, Rizzoli C (2004) Org Lett 6:417PubMedPubMedCentralCrossRefGoogle Scholar
  107. 107.
    Benati L, Bencivenni G, Leardini R, Nanni D, Minozzi M, Spagnolo P, Scialpi R, Zanardi G (2006) Org Lett 8:2499PubMedCrossRefGoogle Scholar
  108. 108.
    Narasaka K, Kitamura M (2005) Eur J Org Chem:4505Google Scholar
  109. 109.
    Zard SZ (1996) Synlett 1996:1148CrossRefGoogle Scholar
  110. 110.
    Walton J (2016) Molecules 21:63PubMedPubMedCentralCrossRefGoogle Scholar
  111. 111.
    Walton J (2016) Molecules 21:660CrossRefGoogle Scholar
  112. 112.
    Jackman MM, Cai Y, Castle SL (2017) Synthesis 49:1785CrossRefGoogle Scholar
  113. 113.
    McBurney RT, Walton JC (2013) J Am Chem Soc 135:7349PubMedPubMedCentralCrossRefGoogle Scholar
  114. 114.
    Le Tadic-Biadatti M-H, Callier-Dublanchet A-C, Horner JH, Quiclet-Sire B, Zard SZ, Newcomb M (1997) J Org Chem 62:559PubMedCrossRefGoogle Scholar
  115. 115.
    Morimoto T, Nezu T, Achiwa T, Sekia M (1985) J Chem Soc Chem Commun:1584Google Scholar
  116. 116.
    Boivin J, Fouquet E, Zard SZ (1990) Tetrahedron Lett 31:85–88CrossRefGoogle Scholar
  117. 117.
    Brown C, Hudson RF, Record KAF (1978) J Chem Soc Perkin Trans 2:822CrossRefGoogle Scholar
  118. 118.
    Lin X, Stien D, Weinreb SM (1999) Org Lett 1:637PubMedCrossRefGoogle Scholar
  119. 119.
    Lin X, Stien D, Weinreb SM (2000) Tetrahedron Lett 41:2333CrossRefGoogle Scholar
  120. 120.
    Lin X, Artman Iii GD, Stien D, Weinreb SM (2001) Tetrahedron 57:8779CrossRefGoogle Scholar
  121. 121.
    Forrester AR, Gill M, Sadd JS, Thomson RH (1975) J Chem Soc Chem Commun:291Google Scholar
  122. 122.
    Boivin J, Fouquet E, Zard SZ (1991) Tetrahedron Lett 32:4299CrossRefGoogle Scholar
  123. 123.
    Boivin J, Fouquet E, Schiano A-M, Zard SZ (1994) Tetrahedron 50:1769CrossRefGoogle Scholar
  124. 124.
    Jiang H, Studer A (2017) Angew Chem Int Ed 56:12273CrossRefGoogle Scholar
  125. 125.
    Davies J, Sheikh NS, Leonori D (2017) Angew Chem Int Ed 56:13361CrossRefGoogle Scholar
  126. 126.
    Dauncey EM, Marcillo SP, Douglas JJ, Sheikh NS, Leonori D (2018) Angew Chem Int Ed 57:744.
  127. 127.
    Duan X-Y, Zhou N-N, Fang R, Yang X-L, Yu W, Han B (2014) Angew Chem Int Ed 53:3158CrossRefGoogle Scholar
  128. 128.
    Asensio G, Gonzalez-Nunez E, Rodrigo MJ (1987) J Chem Soc Chem Commun:263Google Scholar
  129. 129.
    Xu H-C, Campbell JM, Moeller KD (2014) J Org Chem 79:379PubMedCrossRefGoogle Scholar
  130. 130.
    Zhu L, Xiong P, Mao Z-Y, Wang Y-H, Yan X, Lu X, Xu H-C (2016) Angew Chem Int Ed 55:2226CrossRefGoogle Scholar
  131. 131.
    Folgueiras-Amador AA, Philipps K, Guilbaud S, Poelakker J, Wirth T (2017) Angew Chem Int Ed 56:15446CrossRefGoogle Scholar
  132. 132.
    Choi GJ, Knowles RR (2015) J Am Chem Soc 137:9226PubMedPubMedCentralCrossRefGoogle Scholar
  133. 133.
    Miller DC, Choi GJ, Orbe HS, Knowles RR (2015) J Am Chem Soc 137:13492–13495PubMedPubMedCentralCrossRefGoogle Scholar
  134. 134.
    Choi GJ, Zhu Q, Miller DC, Gu CJ, Knowles RR (2016) Nature 539:268PubMedPubMedCentralCrossRefGoogle Scholar
  135. 135.
    Nguyen LQ, Knowles RR (2016) ACS Catal 6:2894CrossRefGoogle Scholar
  136. 136.
    Gentry EC, Knowles RR (2016) Acc Chem Res 49:1546PubMedPubMedCentralCrossRefGoogle Scholar
  137. 137.
    Mackiewicz P, Furstoss R (1978) Tetrahedron 34:3241CrossRefGoogle Scholar
  138. 138.
    Lessard J, Griller D, Ingold KU (1980) J Am Chem Soc 102:3262CrossRefGoogle Scholar
  139. 139.
    Sutcliffe R, Griller D, Lessard J, Ingold KU (1981) J Am Chem Soc 103:624CrossRefGoogle Scholar
  140. 140.
    Lessard J, Mondon M, Touchard D (1981) Can J Chem 59:431CrossRefGoogle Scholar
  141. 141.
    Chen D-F, Chu JCK, Rovis T (2017) J Am Chem Soc 139:14897PubMedCrossRefGoogle Scholar
  142. 142.
    Czaplyski WL, Na CG, Alexanian EJ (2016) J Am Chem Soc 138:13854CrossRefGoogle Scholar
  143. 143.
    Sutcliffe R, Ingold KU (1982) J Am Chem Soc 104:6071CrossRefGoogle Scholar
  144. 144.
    Horner JH, Musa OM, Bouvier A, Newcomb M (1998) J Am Chem Soc 120:7738CrossRefGoogle Scholar
  145. 145.
    Chow YL, Perry RA (1985) Can J Chem 63:2203CrossRefGoogle Scholar
  146. 146.
    Clark AJ, Deeth RJ, Samuel CJ, Wongtap H (1999) Synlett:444Google Scholar
  147. 147.
    Clark AJ, Peacock JL (1998) Tetrahedron Lett 39:6029CrossRefGoogle Scholar
  148. 148.
    Chen Q, Shen M, Tang Y, Li C (2005) Org Lett 7:1625PubMedCrossRefGoogle Scholar
  149. 149.
    Esker JL, Newcomb M (1992) Tetrahedron Lett 33:5913CrossRefGoogle Scholar
  150. 150.
    Boivin J, Callier-Dublanchet A-C, Quiclet-Sire B, Schiano A-M, Zard SZ (1995) Tetrahedron 51:6517CrossRefGoogle Scholar
  151. 151.
    Cassayre J, Gagosz F, Zard SZ (2002) Angew Chem Int Ed 41:1783–1785CrossRefGoogle Scholar
  152. 152.
    Sharp LA, Zard SZ (2006) Org Lett 8:831PubMedCrossRefGoogle Scholar
  153. 153.
    Callier-Dublanchet A-C, Cassayre J, Gagosz F, Quiclet-Sire B, Sharp LA, Zard SZ (2008) Tetrahedron 64:4803CrossRefGoogle Scholar
  154. 154.
    Biechy A, Hachisu S, Quiclet-Sire B, Ricard L, Zard SZ (2008) Angew Chem Int Ed 47:1436CrossRefGoogle Scholar
  155. 155.
    Biechy A, Hachisu S, Quiclet-Sire B, Ricard L, Zard SZ (2009) Tetrahedron 65:6730CrossRefGoogle Scholar
  156. 156.
    Han G, Liu Y, Wang Q (2013) Org Lett 15:5334PubMedPubMedCentralCrossRefGoogle Scholar
  157. 157.
    Moutrille C, Zard SZ (2004) Chem Commun:1848Google Scholar
  158. 158.
    Zhuang S, Liu K, Li C (2011) J Org Chem 76:8100PubMedCrossRefGoogle Scholar
  159. 159.
    Yu Y-Y, Fu Y, Xie M, Liu L, Guo Q-X (2007) J Org Chem 72:8025PubMedCrossRefGoogle Scholar
  160. 160.
    Yuan X, Liu K, Li C (2008) J Org Chem 73:6166PubMedCrossRefGoogle Scholar
  161. 161.
    Clark AJ, Peacock JL (1998) Tetrahedron Lett 39:1265CrossRefGoogle Scholar
  162. 162.
    Clark AJ, Filik RP, Paecock JL, Thomas GH (1999) Synlett:441Google Scholar
  163. 163.
    Davies J, Svejstrup TD, Fernandez Reina D, Sheikh NS, Leonori D (2016) J Am Chem Soc 138:8092PubMedPubMedCentralCrossRefGoogle Scholar
  164. 164.
    Reina DF, Dauncey EM, Morcillo SP, Svejstrup TD, Popescu MV, Douglas JJ, Sheikh NS, Leonori D (2017) Eur J Org Chem:2108Google Scholar
  165. 165.
    Wu K, Du Y, Wang T (2017) Org Lett 19:5669PubMedCrossRefGoogle Scholar
  166. 166.
    Ren X, Guo Q, Chen J, Xie H, Xu Q, Lu Z (2016) Chem A Eur J 22:18695CrossRefGoogle Scholar
  167. 167.
    Weinberg DR, Gagliardi CJ, Hull JF, Murphy CF, Kent CA, Westlake BC, Paul A, Ess DH, McCafferty DG, Meyer TJ (2012) Chem Rev 112:4016PubMedCrossRefGoogle Scholar
  168. 168.
    Migliore A, Polizzi NF, Therien MJ, Beratan DN (2014) Chem Rev 114:3381PubMedPubMedCentralCrossRefGoogle Scholar
  169. 169.
    Siewert I (2015) Chem A Eur J 21:15078CrossRefGoogle Scholar
  170. 170.
    Hoffmann N (2017) Eur J Org Chem:1982Google Scholar
  171. 171.
    Li S-Q, Xiong P, Zhu L, Qian X-Y, Xu H-C (2016) Eur J Org Chem:3449Google Scholar
  172. 172.
    Xiong P, Xu F, Qian X-Y, Yohannes Y, Song J, Lu X, Xu H-C (2016) Chem A Eur J 22:4379CrossRefGoogle Scholar
  173. 173.
    Nicolaou KC, Baran PS, Kranich R, Zhong Y-L, Sugita K, Zou N (2001) Angew Chem Int Ed 40:202CrossRefGoogle Scholar
  174. 174.
    Hou Z-W, Mao Z-Y, Song J, Xu H-C (2017) ACS Catal 7:5810CrossRefGoogle Scholar
  175. 175.
    Hofmann AW (1883) Ber 16:558Google Scholar
  176. 176.
    Gutekunst WR, Baran PS (2011) Chem Soc Rev 40:1976PubMedCrossRefGoogle Scholar
  177. 177.
    Jeffrey JL, Sarpong R (2013) Chem Sci 4:4092CrossRefGoogle Scholar
  178. 178.
    Löffler K, Freytag C (1909) Ber 42:3727Google Scholar
  179. 179.
    Majetich G, Wheless K (1995) Tetrahedron 51:7095CrossRefGoogle Scholar
  180. 180.
    Feray L, Kuznetsov N, Renaud P (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, vol 2. Wiley-VCH, Weinheim, p 246Google Scholar
  181. 181.
    Corey EJ, Hertler WR (1958) J Am Chem Soc 80:2903CrossRefGoogle Scholar
  182. 182.
    Buchschacher P, Kalvoda J, Arigoni D, Jeger O (1958) J Am Chem Soc 80:2905CrossRefGoogle Scholar
  183. 183.
    Qin Q, Yu S (2015) Org Lett 17:1894PubMedPubMedCentralCrossRefGoogle Scholar
  184. 184.
    Hernandez R, Rivera A, Salazar JA, Suarez E (1980) J Chem Soc Chem Commun:958Google Scholar
  185. 185.
    Betancor C, Concepcion JI, Hernandez R, Salazar JA, Suarez E (1983) J Org Chem 48:4430CrossRefGoogle Scholar
  186. 186.
    Freire R, Martın A, Pérez-Martın I, Suárez E (2002) Tetrahedron Lett 43:5113CrossRefGoogle Scholar
  187. 187.
    Francisco CG, Herrera AJ, Martín Á, Pérez-Martín I, Suárez E (2007) Tetrahedron Lett 48:6384CrossRefGoogle Scholar
  188. 188.
    Martín A, Pérez-Martín I, Suárez E (2009) Tetrahedron 65:6147CrossRefGoogle Scholar
  189. 189.
    León EI, Martín Á, Pérez-Martín I, Suárez E (2011) Eur J Org Chem:7339Google Scholar
  190. 190.
    Reddy LR, Reddy BVS, Corey EJ (2006) Org Lett 8:2819PubMedCrossRefGoogle Scholar
  191. 191.
    Henry DJ, Sullivan MB, Radom L (2003) J Chem Phys 118:4849CrossRefGoogle Scholar
  192. 192.
    Šakić D, Zipse H (2016) Adv Synth Catal 358:3983CrossRefGoogle Scholar
  193. 193.
    Koag M, Lee S (2011) Org Lett 13:4766PubMedCrossRefGoogle Scholar
  194. 194.
    Kou Y, Koag MC, Cheun Y, Shin A, Lee S (2012) Steroids 77:1069PubMedCrossRefGoogle Scholar
  195. 195.
    Martínez C, Muñiz K (2015) Angew Chem Int Ed 54:8287CrossRefGoogle Scholar
  196. 196.
    Wappes EA, Fosu SC, Chopko TC, Nagib DA (2016) Angew Chem Int Ed 55:9974CrossRefGoogle Scholar
  197. 197.
    Nicewicz DA, Nguyen TM (2014) ACS Catal 4:355CrossRefGoogle Scholar
  198. 198.
    Becker P, Duhamel T, Stein CJ, Reiher M, Muñiz K (2017) Angew Chem Int Ed 56:8004CrossRefGoogle Scholar
  199. 199.
    Johnson RA, Greene FD (1975) J Org Chem 40:2186CrossRefGoogle Scholar
  200. 200.
    Petterson RC, Wambsgans A (1964) J Am Chem Soc 86:1648CrossRefGoogle Scholar
  201. 201.
    Barton DHR, Beckwith ALJ, Goosen A (1965) J Chem Soc:181Google Scholar
  202. 202.
    Hernández R, Medina MC, Salazar JA, Suárez E, Prangé T (1987) Tetrahedron Lett 28:2533CrossRefGoogle Scholar
  203. 203.
    Martín A, Pérez-Martín I, Suárez E (2005) Org Lett 7:2027PubMedCrossRefGoogle Scholar
  204. 204.
    Wappes EA, Nakafuku KM, Nagib DA (2017) J Am Chem Soc 139:10204PubMedPubMedCentralCrossRefGoogle Scholar
  205. 205.
    Forrester AR, Gill M, Napier RJ, Thomson RH (1979) J Chem Soc Perkin Trans 1:632CrossRefGoogle Scholar
  206. 206.
    Forrester AR, Napier RJ, Thomson RH (1981) J Chem Soc Perkin Trans 1:984CrossRefGoogle Scholar
  207. 207.
    Leca D, Fensterbank L, Lacote E, Malacria M (2005) Chem Soc Rev 34:858PubMedCrossRefGoogle Scholar
  208. 208.
    Espinal-Viguri M, King AK, Lowe JP, Mahon MF, Webster RL (2016) ACS Catal 6:7892CrossRefGoogle Scholar
  209. 209.
    Davies AG, Parrott MJ, Roberts BP (1974) J Chem Soc Chem Commun:27Google Scholar
  210. 210.
    Davies AG, Parrott MJ, Roberts BP (1976) J Chem Soc Perkin Trans 2:1066CrossRefGoogle Scholar
  211. 211.
    Issleib K, Kühne U, Krech F (1985) Z Anorg Allg Chem 523:7CrossRefGoogle Scholar
  212. 212.
    Krech F, Issleib K, Zschunke A, Mügge C, Skvorcov S (1991) Z Anorg Allg Chem 594:66CrossRefGoogle Scholar
  213. 213.
    Krech F, Issleib K, Zschunke A (1991) Z Anorg Allg Chem 600:195CrossRefGoogle Scholar
  214. 214.
    Krech F, Zschunke A, Issleib K (1993) Z Anorg Allg Chem 619:989CrossRefGoogle Scholar
  215. 215.
    Krauss B, Mügge C, Zschunke A, Krech F, Flock M (2002) Z Anorg Allg Chem 628:580CrossRefGoogle Scholar
  216. 216.
    Pellon J (1961) J Am Chem Soc 83:1915CrossRefGoogle Scholar
  217. 217.
    Robertson A, Bradaric C, Frampton CS, McNulty J, Capretta A (2001) Tetrahedron Lett 42:2609CrossRefGoogle Scholar
  218. 218.
    Ullrich V, Brugger R (1994) Angew Chem Int Ed 33:1911CrossRefGoogle Scholar
  219. 219.
    Beckwith ALJ, Hay BP (1988) J Am Chem Soc 110:4415CrossRefGoogle Scholar
  220. 220.
    Beckwith ALJ, Hay BP, Williams GM (1989) J Chem Soc Chem Commun:1202Google Scholar
  221. 221.
    Barton DHR, Beaton JM, Geller LE, Pechet MM (1961) J Am Chem Soc 83:4076CrossRefGoogle Scholar
  222. 222.
    Walling C, Padwa A (1963) J Am Chem Soc 85:1593CrossRefGoogle Scholar
  223. 223.
    Zlotorzynska M, Zhai H, Sammis GM (2008) Org Lett 10:5083PubMedPubMedCentralCrossRefGoogle Scholar
  224. 224.
    Rueda-Becerril M, Leung JCT, Dunbar CR, Sammis GM (2011) J Org Chem 76:7720PubMedPubMedCentralCrossRefGoogle Scholar
  225. 225.
    Yokota M, Toyota M, Ihara M (2003) Chem Commun:422Google Scholar
  226. 226.
    Hartung J, Kneuer R, Rummey C, Bringmann G (2004) J Am Chem Soc 126:12121PubMedCrossRefGoogle Scholar
  227. 227.
    Schuch D, Fries P, Dönges M, Pérez BM, Hartung J (2009) J Am Chem Soc 131:12918PubMedCrossRefGoogle Scholar
  228. 228.
    Fries P, Halter D, Kleinschek A, Hartung J (2011) J Am Chem Soc 133:3906PubMedCrossRefGoogle Scholar
  229. 229.
    Hartung J, Gallou F (1995) J Org Chem 60:6706CrossRefGoogle Scholar
  230. 230.
    Guindon Y, Denis RC (1998) Tetrahedron Lett 39:339CrossRefGoogle Scholar
  231. 231.
    Hartung J (2001) Eur J Org Chem:619Google Scholar
  232. 232.
    Rieke RD, Moore NA (1969) Tetrahedron Lett 10:2035CrossRefGoogle Scholar
  233. 233.
    Hartung J, Daniel K, Gottwald T, Grob A, Schneiders N (2006) Org Biomol Chem 4:2313PubMedCrossRefGoogle Scholar
  234. 234.
    De Luca L, Giacomelli G, Porcu G, Taddei M (2001) Org Lett 3:855PubMedCrossRefGoogle Scholar
  235. 235.
    Hartung J, Kneuer R, Kopf TM, Schmidt P (2001) Compt Rend Acad Sci Series IIC Chem 4:649Google Scholar
  236. 236.
    Hartung J, Gottwald T, Špehar K (2003) Synlett:227Google Scholar
  237. 237.
    Hartung J, Schur C, Kempter I, Gottwald T (2010) Tetrahedron 66:1365CrossRefGoogle Scholar
  238. 238.
    Schur C, Becker N, Bergsträßer U, Gottwald T, Hartung J (2011) Tetrahedron 67:2338CrossRefGoogle Scholar
  239. 239.
    Gottwald T, Greb M, Hartung J (2004) Synlett:65Google Scholar
  240. 240.
    Hartung J, Kneuer R, Laug S, Schmidt P, Špehar K, Svoboda I, Fuess H (2003) Eur J Org Chem:4033Google Scholar
  241. 241.
    Hartung J, Daniel K, Bergsträßer U, Kempter I, Schneiders N, Danner S, Schmidt P, Svoboda I, Fuess H (2009) Eur J Org Chem:4135Google Scholar
  242. 242.
    Hartung J, Schwarz M, Svoboda I, Fuess H, Duarte MT (1999) Eur J Org Chem:1275Google Scholar
  243. 243.
    Schur C, Kempter I, Hartung J (2012) Organic Synth 89:409CrossRefGoogle Scholar
  244. 244.
    Ishibashi H (2006) Chem Rec 6:23PubMedCrossRefGoogle Scholar
  245. 245.
    Barton DHR, Motherwell RSH, Motherwell WB (1981) J Chem Soc Perkin Trans 1:2363CrossRefGoogle Scholar
  246. 246.
    Johns A, Murphy JA (1988) Tetrahedron Lett 29:837CrossRefGoogle Scholar
  247. 247.
    Johns A, Murphy JA, Sherburn MS (1989) Tetrahedron 45:7835CrossRefGoogle Scholar
  248. 248.
    Gash RC, MacCorquodale F, Walton JC (1989) Tetrahedron 45:5531CrossRefGoogle Scholar
  249. 249.
    Dénès F, Beaufils F, Renaud P (2008) Synlett:2389Google Scholar
  250. 250.
    Inoki S, Mukaiyama T (1990) Chem Lett 19:67CrossRefGoogle Scholar
  251. 251.
    Teruaki M, Tohru Y (1995) Bull Chem Soc Jpn 68:17CrossRefGoogle Scholar
  252. 252.
    Wang Z-M, Tian S-K, Shi M (1999) Tetrahedron Lett 40:977CrossRefGoogle Scholar
  253. 253.
    Wang Z-M, Tian S-K, Shi M (1999) Tetrahedron Asymmetry 10:667CrossRefGoogle Scholar
  254. 254.
    Menendez Perez B, Schuch D, Hartung J (2008) Org Biomol Chem 6:3532PubMedCrossRefGoogle Scholar
  255. 255.
    Heusler K, Kalvoda J (1964) Angew Chem Int Ed 3:525CrossRefGoogle Scholar
  256. 256.
    Mihailović ML, Čeković Ž (1970) Synthesis 1970:209CrossRefGoogle Scholar
  257. 257.
    Kalvoda J, Heusler K (1971) Synthesis 1971:501CrossRefGoogle Scholar
  258. 258.
    Brun P, Waegell B (1976) Tetrahedron 32:517CrossRefGoogle Scholar
  259. 259.
    Čeković Ž (2003) Tetrahedron 59:8073CrossRefGoogle Scholar
  260. 260.
    Togo H (2004) In: Advanced free radical reactions for organic synthesis. Elsevier Science, Amsterdam, p 171CrossRefGoogle Scholar
  261. 261.
    Čeković Ž (2005) J Serb Chem Soc 70:287CrossRefGoogle Scholar
  262. 262.
    Akhtar M (2007) In: Advances in photochemistry. Wiley, New York, p 263CrossRefGoogle Scholar
  263. 263.
    Petrovic G, Čeković Ž (1999) Tetrahedron 55:1377CrossRefGoogle Scholar
  264. 264.
    Petrovic G, Čeković Ž (2000) Org Lett 2:3769PubMedCrossRefGoogle Scholar
  265. 265.
    Petrovic G, Saicic NR, Čeković Ž (2003) Helv Chim Acta 86:3179CrossRefGoogle Scholar
  266. 266.
    Petrovic G, Čeković Ž (2003) J Serb Chem Soc 68:313CrossRefGoogle Scholar
  267. 267.
    Petrovic G, Čeković Ž (2004) Synthesis:1671Google Scholar
  268. 268.
    Paul H, Small RD, Scaiano JC (1978) J Am Chem Soc 100:4520CrossRefGoogle Scholar
  269. 269.
    Wong SK (1979) J Am Chem Soc 101:1235CrossRefGoogle Scholar
  270. 270.
    Nechab M, Mondal S, Bertrand MP (2014) Chem A Eur J 20:16034CrossRefGoogle Scholar
  271. 271.
    Barton DHR, Beaton JM, Geller LE, Pechet MM (1960) J Am Chem Soc 82:2640CrossRefGoogle Scholar
  272. 272.
    Barton DHR, Beaton JM (1960) J Am Chem Soc 82:2641CrossRefGoogle Scholar
  273. 273.
    Akhtar M, Barton DHR, Sammes PG (1965) J Am Chem Soc 87:4601CrossRefGoogle Scholar
  274. 274.
    Akhtar M, Barton DHR, Sammes PG (1964) J Am Chem Soc 86:3394CrossRefGoogle Scholar
  275. 275.
    Walling C, Padwa A (1963) J Am Chem Soc 85:1597CrossRefGoogle Scholar
  276. 276.
    Danishefsky SJ, Armistead DM, Wincott FE, Selnick HG, Hungate R (1987) J Am Chem Soc 109:8117CrossRefGoogle Scholar
  277. 277.
    Francisco CG, Freire R, Hernández R, Medina MC, Suárez E (1983) Tetrahedron Lett 24:4621CrossRefGoogle Scholar
  278. 278.
    Concepción JI, Francisco CG, Hernández R, Salazar JA, Suárez E (1984) Tetrahedron Lett 25:1953CrossRefGoogle Scholar
  279. 279.
    Kay IT, Bartholomew D (1984) Tetrahedron Lett 25:2035CrossRefGoogle Scholar
  280. 280.
    Francisco CG, Herrera AJ, Kennedy AR, Melián D, Suárez E (2002) Angew Chem Int Ed 41:856CrossRefGoogle Scholar
  281. 281.
    Martín A, Pérez-Martín I, Quintanal LM, Suárez E (2007) Org Lett 9:1785PubMedCrossRefGoogle Scholar
  282. 282.
    Guyenne S, León EI, Martín A, Pérez-Martín I, Suárez E (2012) J Org Chem 77:7371PubMedCrossRefGoogle Scholar
  283. 283.
    Alvarez-Dorta D, León EI, Kennedy AR, Martín A, Pérez-Martín I, Suárez E (2015) Angew Chem Int Ed 54:3674CrossRefGoogle Scholar
  284. 284.
    Alvarez-Dorta D, León EI, Kennedy AR, Martín A, Pérez-Martín I, Suárez E (2016) J Org Chem 81:11766PubMedCrossRefGoogle Scholar
  285. 285.
    Tsunoi S, Ryu I, Okuda T, Tanaka M, Komatsu M, Sonoda N (1998) J Am Chem Soc 120:8692CrossRefGoogle Scholar
  286. 286.
    Porter NA, Caldwell SE, Mills KA (1995) Lipids 30:277PubMedCrossRefGoogle Scholar
  287. 287.
    Yin H, Havrilla CM, Gao L, Morrow JD, Porter NA (2003) J Biol Chem 278:16720PubMedCrossRefGoogle Scholar
  288. 288.
    Yin H, Xu L, Porter NA (2011) Chem Rev 111:5944PubMedCrossRefGoogle Scholar
  289. 289.
    Porter NA (2013) J Org Chem 78:3511PubMedPubMedCentralCrossRefGoogle Scholar
  290. 290.
    Yin H, Morrow JD, Porter NA (2004) J Biol Chem 279:3766PubMedCrossRefGoogle Scholar
  291. 291.
    Funk CD (2001) Science 294:1871PubMedCrossRefGoogle Scholar
  292. 292.
    Gardner HW (1989) Free Rad. Biol Med 7:65Google Scholar
  293. 293.
    Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai H-H, Dey SK, Porter NA, Morrow JD (2003) J Biol Chem 278:28479PubMedCrossRefGoogle Scholar
  294. 294.
    Funk MO, Isaac R, Porter NA (1975) J Am Chem Soc 97:1281PubMedCrossRefGoogle Scholar
  295. 295.
    Porter NA, Funk MO (1975) J Org Chem 40:3614PubMedCrossRefGoogle Scholar
  296. 296.
    Kharasch MS, Nudenberg W, Mantell GJ (1951) J Org Chem 16:524CrossRefGoogle Scholar
  297. 297.
    Thaler WA, Oswald AA, Hudson Jr BE (1965) J Am Chem Soc 87:311CrossRefGoogle Scholar
  298. 298.
    Beckwith ALJ, Wagner RD (1979) J Am Chem Soc 101:7099CrossRefGoogle Scholar
  299. 299.
    Roe AN, McPhail AT, Porter NA (1983) J Am Chem Soc 105:1199CrossRefGoogle Scholar
  300. 300.
    Porter NA, Roe AN, McPhail AT (1980) J Am Chem Soc 102:7574CrossRefGoogle Scholar
  301. 301.
    Beckwith ALJ, Wagner RD (1980) J Chem Soc Chem Commun:485Google Scholar
  302. 302.
    Barker PJ, Beckwith ALJ, Fung Y (1983) Tetrahedron Lett 24:97CrossRefGoogle Scholar
  303. 303.
    Wang X, Ni Z, Lu X, Smith TY, Rodriguez A, Padwa A (1992) Tetrahedron Lett 33:5917CrossRefGoogle Scholar
  304. 304.
    Wang X, Ni Z, Liu X, Hollis A, Blanks H, Rodriguez A, Padwa A (1993) J Org Chem 58:5377CrossRefGoogle Scholar
  305. 305.
    Porter NA, Lehman LS, Weber BA, Smith KJ (1981) J Am Chem Soc 103:6447CrossRefGoogle Scholar
  306. 306.
    Porter NA, Funk MO, Gilmore D, Saac R, Nixon J (1976) J Am Chem Soc 98:6000PubMedCrossRefGoogle Scholar
  307. 307.
    Beckwith ALJ, Schiesser CH (1985) Tetrahedron Lett 26:373CrossRefGoogle Scholar
  308. 308.
    Szpilman AM, Korshin EE, Rozenberg H, Bachi MD (2005) J Org Chem 70:3618PubMedCrossRefGoogle Scholar
  309. 309.
    Bachi MD, Korshin EE (1998) Synlett:122Google Scholar
  310. 310.
    Bachi MD, Korshin EE, Ploypradith P, Cumming JN, Xie S, Shapiro TA, Posner GH (1998) Bioorg Med Lett 8:903CrossRefGoogle Scholar
  311. 311.
    Bachi MD, Korshin EE, Hoos R, Szpilman AM (2000) J Heterocycl Chem 37:639CrossRefGoogle Scholar
  312. 312.
    Szpilman AM, Korshin EE, Hoos R, Posner GH, Bachi MD (2001) J Org Chem 66:6531PubMedCrossRefGoogle Scholar
  313. 313.
    Korshin EE, Hoos R, Szpilman AM, Konstantinovski L, Posner GH, Bachi MD (2002) Tetrahedron 58:2449CrossRefGoogle Scholar
  314. 314.
    Bachi MD, Korshin EE, Hoos R, Szpilman AM, Ploypradith P, Xie S, Shapiro TA, Posner GH (2003) J Med Chem 46:2516PubMedCrossRefGoogle Scholar
  315. 315.
    O’Neill PM, Stocks PA, Pugh MD, Araujo NC, Korshin EE, Bickley JF, Ward SA, Bray PG, Pasini E, Davies J, Verissimo E, Bachi MD (2004) Angew Chem Int Ed 43:4193CrossRefGoogle Scholar
  316. 316.
    Feldman KS, Simpson RE, Parvez M (1986) J Am Chem Soc 108:1328CrossRefGoogle Scholar
  317. 317.
    Feldman KS, Simpson RE (1989) J Am Chem Soc 111:4878Google Scholar
  318. 318.
    Feldman KS, Simpson RE (1989) Tetrahedron Lett 30:6985CrossRefGoogle Scholar
  319. 319.
    Feldman KS (1995) Synlett:217Google Scholar
  320. 320.
    Chong S-S, Fu Y, Liu L, Guo Q-X (2007) J Phys Chem A 111:13112PubMedCrossRefGoogle Scholar
  321. 321.
    Thomas JR (1964) J Am Chem Soc 86:1446CrossRefGoogle Scholar
  322. 322.
    Brokenshire JL, Mendenhall GD, Ingold KU (1971) J Am Chem Soc 93:5278CrossRefGoogle Scholar
  323. 323.
    Li W, Jia P, Han B, Li D, Yu W (2013) Tetrahedron 69:3274CrossRefGoogle Scholar
  324. 324.
    Han B, Yang X-L, Fang R, Yu W, Wang C, Duan X-Y, Liu S (2012) Angew Chem Int Ed 51:8816CrossRefGoogle Scholar
  325. 325.
    Peng X-X, Deng Y-J, Yang X-L, Zhang L, Yu W, Han B (2014) Org Lett 16:4650PubMedCrossRefGoogle Scholar
  326. 326.
    Liu R-H, Wei D, Han B, Yu W (2016) ACS Catal 6:6525CrossRefGoogle Scholar
  327. 327.
    Kooyman EC (1967) Pure Appl Chem 15:81CrossRefGoogle Scholar
  328. 328.
    Griesbaum K (1970) Angew Chem Int Ed 9:273CrossRefGoogle Scholar
  329. 329.
    Chatgilialoglu C, Guerra M (1993) In: Patai S, Rappoport Z (eds) Supplement S: the chemistry of sulfur-containing functional groups. Wiley, Chichester, p 363Google Scholar
  330. 330.
    Chatgilialoglu C, Bertrand MP, Ferreri C (1999) In: Alfassi ZB (ed) S-centered radicals. Wiley, Chichester, p 310Google Scholar
  331. 331.
    von Sonntag C (1990) In: Chatgilialoglu C, Asmus K-D (eds) Sulfur-centered reactive intermediates in chemistry and biology. Plenum Press, New York, p 359Google Scholar
  332. 332.
    Voronkov MG, Deryagina EN (1990) Russ Chem Rev 59:778CrossRefGoogle Scholar
  333. 333.
    Dénès F, Pichowicz M, Povie G, Renaud P (2014) Chem Rev 114:2587PubMedCrossRefGoogle Scholar
  334. 334.
    Scanlan ME, Corcé V, Malone A (2014) Molecules 19:19137PubMedCrossRefPubMedCentralGoogle Scholar
  335. 335.
    Massi A, Nanni D (2012) Org Biomol Chem 10:3791PubMedCrossRefPubMedCentralGoogle Scholar
  336. 336.
    ten Brummelhuis N, Schlaad H (2012) In: Chatgilialoglu C, Studer A (eds) Encyclopedia of radicals in chemistry, biology and materials, polymers and materials, vol 4. Wiley, Chichester, p 2017Google Scholar
  337. 337.
    Wille U (2013) Chem Rev 113:813CrossRefPubMedGoogle Scholar
  338. 338.
    McSweeney L, Dénès F, Scanlan EM (2016) Eur J Org Chem:2080Google Scholar
  339. 339.
    Chatgilialoglu C, Ferreri C, Melchiorre M, Sansone A, Torreggiani A (2014) Chem Rev 114:255PubMedCrossRefGoogle Scholar
  340. 340.
    Huston P, Espenson JH, Bakac A (1992) Inorg Chem 31:720CrossRefGoogle Scholar
  341. 341.
    Ito O (1995) Res Chem Intermed 21:69CrossRefGoogle Scholar
  342. 342.
    Walling C, Helmreich W (1959) J Am Chem Soc 81:1144CrossRefGoogle Scholar
  343. 343.
    Heiba E-AI, Dessau RM (1967) J Org Chem 32:3837CrossRefGoogle Scholar
  344. 344.
    Surzur J-M, Crozet MP, Dupuy C (1967) Compt Rend Acad Sci Série C 264:610Google Scholar
  345. 345.
    Surzur J-M, Crozet MP, Dupuy C (1971) Tetrahedron Lett 12:2025CrossRefGoogle Scholar
  346. 346.
    Crozet MP, Surzur J-M, Dupuy C (1971) Tetrahedron Lett 12:2031CrossRefGoogle Scholar
  347. 347.
    Surzur J-M, Nouguier R, Crozet MP, Dupuy C (1971) Tetrahedron Lett 12:2035CrossRefGoogle Scholar
  348. 348.
    Bastien G, Surzur J-M (1979) Bull Soc Chim Fr:601Google Scholar
  349. 349.
    Bastien G, Crozet MP, Flesia E, Surzur J-M (1979) Bull Soc Chim Fr:606Google Scholar
  350. 350.
    Surzur J M; Abramovitch R A, Ed.; Plenum Press: New York, 1982; 2, p 121Google Scholar
  351. 351.
    Nouguier R, Surzur JM (1976) Tetrahedron 32:2001CrossRefGoogle Scholar
  352. 352.
    Surzur J-M, Crozet MP (1969) Compt Rend Acad Sci 268C:2109Google Scholar
  353. 353.
    Kaafarani M, Crozet MP, Surzur J-M (1981) Bull Soc Chim Fr II:449Google Scholar
  354. 354.
    Crozet MP, Kaafarani M, Kassar W, Surzur J-M (1982) Tetrahedron Lett 23:5039CrossRefGoogle Scholar
  355. 355.
    Crozet MP, Kaafarani M, Surzur J-M (1984) Bull Soc Chim Fr II:390Google Scholar
  356. 356.
    Crozet MP, Kassar W (1985) Compt Rend Acad Sci 300:99Google Scholar
  357. 357.
    Kaafarani M, Crozet MP, Surzur J-M (1987) Bull Soc Chim Fr:885Google Scholar
  358. 358.
    Makisumi Y, Murabayashi A (1969) Tetrahedron Lett 10:2449CrossRefGoogle Scholar
  359. 359.
    Makisumi Y, Murabayashi A (1969) Tetrahedron Lett 10:2453CrossRefGoogle Scholar
  360. 360.
    Meyers CY, Rinaldi C, Banoli L (1963) J Org Chem 28:2440CrossRefGoogle Scholar
  361. 361.
    Kwart H, Evans R (1966) J Org Chem 31:413CrossRefGoogle Scholar
  362. 362.
    Maki Y, Sako M (1976) Tetrahedron Lett 17:4291CrossRefGoogle Scholar
  363. 363.
    Maki Y, Sako M (1978) J Chem Soc Chem Commun:836Google Scholar
  364. 364.
    Gordon EM, Cimarusti CM (1977) Tetrahedron Lett 18:3425CrossRefGoogle Scholar
  365. 365.
    Cabri W, Candiani I, Bedeschi A (1992) Tetrahedron Lett 33:4783CrossRefGoogle Scholar
  366. 366.
    Takabe K, Katagiri T, Tanaka S (1970) Tetrahedron Lett 11:4805CrossRefGoogle Scholar
  367. 367.
    Malone A, Scanlan EM (2013) Org Lett 15:504PubMedCrossRefGoogle Scholar
  368. 368.
    Malone A, Scanlan EM (2013) J Org Chem 78:10917PubMedCrossRefGoogle Scholar
  369. 369.
    Corce V, McSweeney L, Malone A, Scanlan EM (2015) Chem Commun 51:8672CrossRefGoogle Scholar
  370. 370.
    Aimetti AA, Shoemaker RK, Lin C-C, Anseth KS (2010) Chem Commun 46:4061CrossRefGoogle Scholar
  371. 371.
    Ichinose Y, Wakamatsu K, Nozaki K, Birbaum J-L, Oshima K, Utimoto K (1987) Chem Lett 16:1647Google Scholar
  372. 372.
    Benati L, Montevecchi PC, Spagnolo P (1991) J Chem Soc Perkin Trans 1:2103CrossRefGoogle Scholar
  373. 373.
    Benati L, Montevecchi PC, Spagnolo P (1992) J Chem Soc Perkin Trans 1:1659CrossRefGoogle Scholar
  374. 374.
    Melandri D, Montevecchi PC, Navacchia ML (1999) Tetrahedron 55:12227CrossRefGoogle Scholar
  375. 375.
    Sukhomazova EN, Russavskaya NV, Kozchevin NA, Deryagina EN, Voronkov MG (1989) Zh Org Khim 25:1506Google Scholar
  376. 376.
    Benati L, Capella L, Montevecchi PC, Spagnolo P (1994) J Org Chem 59:2818CrossRefGoogle Scholar
  377. 377.
    Montevecchi PC, Navacchia ML (1997) J Org Chem 62:5600CrossRefGoogle Scholar
  378. 378.
    Montevecchi PC, Navacchia ML, Spagnolo P (1998) Tetrahedron 54:8207CrossRefGoogle Scholar
  379. 379.
    Benati L, Capella L, Montevecchi PC, Spagnolo P (1995) J Org Chem 60:7941CrossRefGoogle Scholar
  380. 380.
    Camaggi CM, Leardini R, Nanni D, Zanardi G (1998) Tetrahedron 54:5587CrossRefGoogle Scholar
  381. 381.
    Nanni D, Calestani G, Leardini R, Zanardi G (2000) Eur J Org Chem:707Google Scholar
  382. 382.
    Schiesser CH, Wild LM (1999) J Org Chem 64:1131CrossRefGoogle Scholar
  383. 383.
    Harrowven DC, Hannam JC, Lucas MC, Newman NA, Howes PD (2000) Tetrahedron Lett 41:9345CrossRefGoogle Scholar
  384. 384.
    James P, Schenk K, Landais Y (2006) J Org Chem 71:3630PubMedCrossRefGoogle Scholar
  385. 385.
    Kamimura A, Miyazaki K, Yamane Y, Yo R, Ishikawa S, Uno H, Sumimoto M (2013) J Org Chem 78:7816PubMedCrossRefGoogle Scholar
  386. 386.
    Padwa A, Nimmesgern H, Wong GSK (1985) J Org Chem 50:5620CrossRefGoogle Scholar
  387. 387.
    Kipping FS, Pope WJ (1895) J Chem Soc Trans 67:371CrossRefGoogle Scholar
  388. 388.
    Culshaw PN, Walton JC (1990) Tetrahedron Lett 31:6433CrossRefGoogle Scholar
  389. 389.
    Lewis FW, Egron G, Grayson DH (2009) Tetrahedron Asymmetry 20:1531CrossRefGoogle Scholar
  390. 390.
    Bertrand F, Le Guyader F, Liguori L, Ouvry G, Quiclet-Sire B, Seguin S, Zard SZ (2001) Compt Rend Acad Sci Series IIC Chem 4:547Google Scholar
  391. 391.
    Fischer H (2001) Chem Rev 101:3581PubMedCrossRefGoogle Scholar
  392. 392.
    Studer A (2001) Chem A Eur J 7:1159CrossRefGoogle Scholar
  393. 393.
    Crease AE, Johnson MD (1978) J Am Chem Soc 100:8013CrossRefGoogle Scholar
  394. 394.
    Johnson MD, Derenne S (1985) J Organomet Chem 286:c47CrossRefGoogle Scholar
  395. 395.
    Bougeard P, Johnson MD, Lampman GM (1982) J Chem Soc Perkin Trans 1:849CrossRefGoogle Scholar
  396. 396.
    Crich D, Hutton TK, Ranganathan K (2005) J Org Chem 70:7672PubMedCrossRefGoogle Scholar
  397. 397.
    Aitken HM, Hancock AN, Schiesser CH (2012) Chem Commun 48:8326CrossRefGoogle Scholar
  398. 398.
    Ashcroft MR, Bougeard P, Bury A, Cooksey CJ, Johnson MD, Hungerford JM, Lampman GM (1984) J Org Chem 49:1751CrossRefGoogle Scholar
  399. 399.
    Culshaw PN, Walton JC (1991) J Chem Soc Perkin Trans 2:1201CrossRefGoogle Scholar
  400. 400.
    Xiao X, Xu Z, Zeng Q-D, Chen X-B, Ji W-H, Han Y, Wu P, Ren J, Zeng B-B (2015) Chem A Eur J 21:8351CrossRefGoogle Scholar
  401. 401.
    Orlov YD, Turovtsev VV, Stepnikov IV, Kizin AN, Lebedev YA (2004) Russ Chem Bull 53:1635CrossRefGoogle Scholar
  402. 402.
    Nogueira CW, Zeni G, Rocha JBT (2004) Chem Rev 104:6255PubMedCrossRefGoogle Scholar
  403. 403.
    Bhuyan BJ, Mugesh G (2011) In: Organoselenium chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, p 361Google Scholar
  404. 404.
    Harwood LM, Moody CJ (1999) In: Back TG (ed) The practical approach in chemistry series: organoselenium chemistry. Oxford University Press, New York, NYGoogle Scholar
  405. 405.
    Wirth T (ed) (2012) Organoselenium chemistry: synthesis and reactions. Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimGoogle Scholar
  406. 406.
    Bowman WR (2011) In: Organoselenium chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, p 111Google Scholar
  407. 407.
    Ogawa A, Yokoyama H, Yokoyama K, Masawaki T, Kambe N, Sonoda N (1991) J Org Chem 56:5721CrossRefGoogle Scholar
  408. 408.
    Crich D, Jiao X-Y, Yao Q, Harwood JS (1996) J Org Chem 61:2368CrossRefGoogle Scholar
  409. 409.
    Newcomb M, Choi S-Y, Horner JH (1999) J Org Chem 64:1225CrossRefGoogle Scholar
  410. 410.
    Crich D, Yao Q (1995) J Org Chem 60:84CrossRefGoogle Scholar
  411. 411.
    Crich D, Mo X-S (1998) J Am Chem Soc 120:8298CrossRefGoogle Scholar
  412. 412.
    Stefani HA, Petragnani N, Ascenso MFC, Zeni G (2003) Synth Commun 33:2161CrossRefGoogle Scholar
  413. 413.
    Kumar S, Johansson H, Engman L, Valgimigli L, Amorati R, Fumo MG, Pedulli GF (2007) J Org Chem 72:2583PubMedCrossRefGoogle Scholar
  414. 414.
    Back TG, Krishna MV (1988) J Org Chem 53:2533CrossRefGoogle Scholar
  415. 415.
    Schiesser CH, Sutej K (1992) Tetrahedron Lett 33:5137CrossRefGoogle Scholar
  416. 416.
    Lyons JE, Schiesser CH, Sutej K (1993) J Org Chem 58:5632CrossRefGoogle Scholar
  417. 417.
    Lucas MA, Schiesser CH (1998) J Org Chem 63:3032CrossRefGoogle Scholar
  418. 418.
    Lucas MA, Schiesser CH (1996) J Org Chem 61:5754CrossRefGoogle Scholar
  419. 419.
    Engman L, Laws MJ, Malmström J, Schiesser CH, Zugaro LM (1999) J Org Chem 64:6764PubMedCrossRefGoogle Scholar
  420. 420.
    Schiesser CH, Zheng S-L (1999) Tetrahedron Lett 40:5095CrossRefGoogle Scholar
  421. 421.
    Lucas MA, Nguyen OTK, Schiesser CH, Zheng S-L (2000) Tetrahedron 56:3995CrossRefGoogle Scholar
  422. 422.
    Al-Maharik N, Engman L, Malmström J, Schiesser CH (2001) J Org Chem 66:6286PubMedCrossRefGoogle Scholar
  423. 423.
    Macdougall PE, Aitken HM, Scammells PJ, Kavanagh Y, Kyne SH, Schiesser CH (2012) Chem Commun 48:9126CrossRefGoogle Scholar
  424. 424.
    Hancock AN, Kavanagh Y, Schiesser CH (2014) Org Chem Front 1:645CrossRefGoogle Scholar
  425. 425.
    Wallace CM, Schiesser CH, Hancock AN (2015) Comp Theor Chem 1068:128CrossRefGoogle Scholar
  426. 426.
    Hancock AN, Lobachevsky S, Haworth NL, Coote ML, Schiesser CH (2015) Org Biomol Chem 13:2310PubMedCrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.CEISAM UMR CNRS 6230Université de NantesNantes, Cedex 3France

Personalised recommendations