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C-Alkylation by Hydrogen Autotransfer Reactions

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Abstract

The development of practical, efficient, and atom-economical methods for the formation of carbon–carbon bonds remains a topic of considerable interest in current synthetic organic chemistry. In this review, we have summarized selected topics from the recent literature with particular emphasis on C-alkylation processes involving hydrogen transfer using alcohols as alkylation reagents. This review includes selected highlights concerning recent progress towards the modification of catalytic systems for the α-alkylation of ketones, nitriles, and esters. Furthermore, we have devoted a significant portion of this review to the methylation of ketones, alcohols, and indoles using methanol. Lastly, we have also documented recent advances in β-alkylation methods involving the dimerization of alcohols (Guerbet reaction), as well as new developments in C-alkylation methods based on sp 3 C–H activation.

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References

  1. Cain D (2000) In: Fleming I, Trost BM (eds) Comprehensive organic synthesis. Pergamon, Oxford, pp 1–63

    Google Scholar 

  2. Reetz MT (1982) Angew Chem Int Ed 21:96–108

    Article  Google Scholar 

  3. Casiraghi G, Battistini L, Curti C, Rassu G, Zanardi F (2011) Chem Rev 111:3076–3091

    Article  CAS  Google Scholar 

  4. Palomo C, Oiarbide M, Garcia JM (2004) Chem Soc Rev 33:65–75

    Article  CAS  Google Scholar 

  5. Arya P, Qin H (2000) Tetrahedron 56:917–928

    Article  CAS  Google Scholar 

  6. Miynarski J, Gut B (2012) Chem Soc Rev 41:587–596

    Article  Google Scholar 

  7. Cheong PHY, Legault CY, Um JM, Celebi-Olcum N, Houk KN (2011) Chem Rev 111:5042–5137

    Article  CAS  Google Scholar 

  8. Shi Z, Yu D (2013) In: Keedij KJ, Poeppelmeier K (eds) Comprehensive inorganic chemistry II, 6th edn. Elsevier, Amsterdam, pp 47–77

    Chapter  Google Scholar 

  9. Chen X, Engle KM, Wang DH, Yu JQ (2009) Angew Chem Int Ed 48:5094–5115

    Article  CAS  Google Scholar 

  10. Guo X, Gu D, Wu Z, Zhang W (2015) Chem Rev 115:1622–1651

    Article  CAS  Google Scholar 

  11. Wendel-Delord J, Glorius F (2013) Nat Chem 5:369–375

    Article  CAS  Google Scholar 

  12. Kozhushkov SI, Ackermann L (2013) Chem Sci 4:886–896

    Article  CAS  Google Scholar 

  13. Arockiam PB, Bruneau C, Dixneuf PH (2012) Chem Rev 112:5879–5918

    Article  CAS  Google Scholar 

  14. Yamaguchi J, Yamaguchi AD, Itami K (2012) Angew Chem Int Ed 51:8960–9009

    Article  CAS  Google Scholar 

  15. Neufeldt SR, Sanford MS (2012) Acc Chem Res 45:936–946

    Article  CAS  Google Scholar 

  16. Song G, Wang F, Li X (2012) Chem Soc Rev 41:3651–3678

    Article  CAS  Google Scholar 

  17. Campell AN, Stahl SS (2012) Acc Chem Res 45:851–863

    Article  CAS  Google Scholar 

  18. Wencel-Deload J, Droege T, Liu F, Glorius F (2011) Chem Soc Rev 40:4740–4761

    Article  CAS  Google Scholar 

  19. Lyons TW, Sanford MS (2010) Chem Rev 110:1147–1169

    Article  CAS  Google Scholar 

  20. Trost BM (1991) Science 254:1471–1477

    Article  CAS  Google Scholar 

  21. Trost BM (2002) Acc Chem Res 35:695–705

    Article  CAS  Google Scholar 

  22. Li C, Trost BM (2008) Proc Natl Acad Sci USA 105:13197–13202

    Article  CAS  Google Scholar 

  23. Guillena G, Ramon DJ, Yus M (2007) Angew Chem Int Ed 46:2358–2364

    Article  CAS  Google Scholar 

  24. Hamid MHSA, Slatford PA, Williams JMJ (2007) Adv Synth Catal 349:1555–1575

    Article  CAS  Google Scholar 

  25. Nixon TD, Whittlesey MK, Williams JMJ (2009) Dalton Trans 753–765

  26. Dobereiner GE, Crabtree RH (2010) Chem Rev 110:681–703

    Article  CAS  Google Scholar 

  27. Bahn S, Imm S, Neubert L, Zhang M, Neumann H, Beller M (2011) ChemCatChem 3:1853–1864

    Article  CAS  Google Scholar 

  28. Marr AC (2012) Catal Sci Technol 2:279–287

    Article  CAS  Google Scholar 

  29. Pan S, Shibata T (2013) ACS Catal 3:704–712

    Article  CAS  Google Scholar 

  30. Mata JA, Hahn FE, Peris E (2014) Chem Sci 5:1723–1732

    Article  CAS  Google Scholar 

  31. Hollman D (2014) ChemSusChem 7:2411–2413

    Article  CAS  Google Scholar 

  32. Guillena G, Ramón D, Yus M (2010) Chem Rev 110:1611–1641

    Article  CAS  Google Scholar 

  33. Watson AJA, Williams JMJ (2010) Science 329:635–636

    Article  CAS  Google Scholar 

  34. Alonso F, Riente P, Yus M (2011) Acc Chem Res 44:379–391

    Article  CAS  Google Scholar 

  35. Fujita K, Yamaguchi R (2005) Synlett 4:560–571

    Google Scholar 

  36. Yamaguchi R, Fujita K, Zhu M (2010) Heterocycles 81:1093–1140

    Article  CAS  Google Scholar 

  37. Obora Y, Ishii Y (2011) Synlett 1:30–51

    Article  CAS  Google Scholar 

  38. Gunanathan C, Milstein D (2013) Science 341:1229712

    Article  CAS  Google Scholar 

  39. Gunanathan C, Milstein D (2011) Acc Chem Res 44:588–602

    Article  CAS  Google Scholar 

  40. Pera-Titus M, Shi F (2014) ChemSusChem 7:2411–2413

    Article  CAS  Google Scholar 

  41. Obora Y, Nakamura K, Hatanaka S (2012) Chem Commun 48:6720–6722

    Article  CAS  Google Scholar 

  42. Obora Y, Hatanaka S, Ishii Y (2009) Org Lett 11:3510–3513

    Article  CAS  Google Scholar 

  43. Hatanaka S, Obora Y, Ishii Y (2010) Chem Eur J 16:1883–1888

    Article  CAS  Google Scholar 

  44. Obora Y, Sawaguchi T, Tsubakimoto K, Yoshida H, Ogawa S, Hatanaka S (2013) Synthesis 45:2115–2119

    Article  CAS  Google Scholar 

  45. Muzart J (2015) Eur J Org Chem 2015:5693–5707

    Article  CAS  Google Scholar 

  46. Díez-Gonzáles S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676

    Article  CAS  Google Scholar 

  47. Suzuki T (2011) Chem Rev 111:1825–1845

    Article  CAS  Google Scholar 

  48. Strakis M, Garcia H (2012) Chem Rev 112:4469–4506

    Article  CAS  Google Scholar 

  49. Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC (2013) Chem Rev 113:6234–6458

    Article  CAS  Google Scholar 

  50. Obora Y (2014) ACS Catal 4:3972–3981

    Article  CAS  Google Scholar 

  51. Cho CS, Kim BT, Kim TJ, Shim SC (2002) Tetrahedron Lett 43:7987–7989

    Article  CAS  Google Scholar 

  52. Cho CS, Shim SC (2006) J Organomet Chem 691:4329–4332

    Article  CAS  Google Scholar 

  53. Martinez R, Brand GJ, Ramón DJ, Yus M (2005) Tetrahedron Lett 46:3683–3686

    Article  CAS  Google Scholar 

  54. Martinez R, Ramón DJ, Yus M (2006) Tetrahedron 62:8988–9001

    Article  CAS  Google Scholar 

  55. Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J (2005) Angew Chem Int Ed 44:6913–6915

    Article  CAS  Google Scholar 

  56. Yamada YMA, Uozumi Y (2006) Org Lett 8:1375–1378

    Article  CAS  Google Scholar 

  57. Taguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y (2004) J Am Chem Soc 126:72–73

    Article  CAS  Google Scholar 

  58. Fujita K, Asai C, Yamaguchi T, Hanasaka F, Yamaguchi R (2005) Org Lett 7:4017–4019

    Article  CAS  Google Scholar 

  59. Viciano M, Sanau M, Peris E (2007) Organometallics 26:6050–6054

    Article  CAS  Google Scholar 

  60. Prades A, Viciano M, Sanau M, Peris E (2008) Organometallics 27:4254–4259

    Article  CAS  Google Scholar 

  61. Da Costa AP, Viciano M, Sanau M, Merino S, Tejeda J, Peris E, Royo R (2008) Organometallics 27:1305–1309

    Article  CAS  Google Scholar 

  62. Satyanarayana P, Reddy GM, Maheswaren H, Kantama ML (2013) Adv Synth Catal 355:1859–1867

    Article  CAS  Google Scholar 

  63. Oded K, Musa S, Gelman D, Blum J (2012) Catal Commun 20:68–72

    Article  CAS  Google Scholar 

  64. Musa S, Shaposhnikov I, Cohen S, Gelman D (2011) Angew Chem Int Ed 50:3533–3537

    Article  CAS  Google Scholar 

  65. Musa S, Fronton S, Vaccaro L, Gelman D (2013) Organometallics 32:3069–3073

    Article  CAS  Google Scholar 

  66. Xu Q, Chen J, Liu Q (2013) Adv Synth Catal 355:697–704

    Article  CAS  Google Scholar 

  67. Musa S, Ackermann L, Gelman D (2013) Adv Synth Catal 355:3077–3080

    Article  CAS  Google Scholar 

  68. Cho CS, Ren WX, Shim SC (2005) Bull Korean Chem Soc 26:1611–1613

    Article  CAS  Google Scholar 

  69. Machemer H (1952) Angew Chem 64:213–220

    Article  CAS  Google Scholar 

  70. Veibel S, Nielsen JI (1967) Tetrahedron 23:1723–1733

    Article  CAS  Google Scholar 

  71. Gregorio G, Pregaglia GF, Ugo R (1972) J Organomet Chem 37:385–387

    Article  CAS  Google Scholar 

  72. Burk PL, Pruett RL, Campo KS (1985) J Mol Catal 33:1–14

    Article  CAS  Google Scholar 

  73. Carlini C, Macinai A, Galletti AMR, Sbrana G (2004) J Mol Catal A Chem 212:65–70

    Article  CAS  Google Scholar 

  74. Pratt EF, Kubler DG (1954) J Am Chem Soc 76:52–56

    Article  CAS  Google Scholar 

  75. Ueda W, Kawahara T, Ohshida T, Morikawa Y (1990) J Chem Soc Chem Commun 1558–1559

  76. Carlini C, Marchionna M, Noviello M, Galetti AMR, Sbrana G, Basile F, Vaccari A (2005) J Mol Catal A 232:13–20

    Article  CAS  Google Scholar 

  77. Cho CS, Kim BT, Kim HS, Kim TJ, Shim SC (2003) Organometallics 22:3608–3610

    Article  CAS  Google Scholar 

  78. Adair GRA, Williams JMJ (2005) Tetrahedron Lett 46:8233–8235

    Article  CAS  Google Scholar 

  79. Martinez R, Ramón DJ, Yus M (2006) Tetrahedron 62:8982–8987

    Article  CAS  Google Scholar 

  80. Matsu-ura T, Sakaguchi S, Obora Y, Ishii Y (2006) J Org Chem 71:8306–8308

    Article  CAS  Google Scholar 

  81. Koda K, Matsu-ura T, Obora Y, Ishii Y (2009) Chem Lett 38:838–839

    Article  CAS  Google Scholar 

  82. Xu C, Goh L, Pullarkat SA (2011) Organometallics 30:6499–6502

    Article  CAS  Google Scholar 

  83. Gong X, Zhang H, Li X (2011) Tetrahedron Lett 52:5596–5600

    Article  CAS  Google Scholar 

  84. Gnanamgari D, Leung CH, Schley ND, Hilton ST, Crabtree RG (2008) Org Biomol Chem 6:4442–4445

    Article  CAS  Google Scholar 

  85. Chang X, Chuan L, Yongxin L, Pullarkat SA (2012) Tetrahedron Lett 53:1450–1455

    Article  CAS  Google Scholar 

  86. Cheung H, Lee T, Lui H, Yeung C, Lau C (2008) Adv Synth Catal 350:2975–2983

    Article  CAS  Google Scholar 

  87. Kose O, Saito S (2010) Org Biomol Chem 8:896–900

    Article  CAS  Google Scholar 

  88. Liao S, Yu K, Li Q, Tian H, Zhang Z, Yu X, Xu Q (2012) Org Biomol Chem 10:2973–2978

    Article  CAS  Google Scholar 

  89. Miura T, Kose O, Li F, Kai S, Saito S (2011) Chem Eur J 17:11146–11151

    Article  CAS  Google Scholar 

  90. Yang J, Liu X, Meng D, Chen H, Zong Z, Feng T, Sun K (2012) Adv Synth Catal 354:328–334

    Article  CAS  Google Scholar 

  91. Kawahara R, Fujita K, Yamaguchi R (2010) J Am Chem Soc 132:15108–15111

    Article  CAS  Google Scholar 

  92. Kawahara R, Fujita K, Yamaguchi R (2011) Adv Synth Catal 353:1161–1168

    Article  CAS  Google Scholar 

  93. Fujita K, Yamamoto K, Yamaguchi R (2002) Org Lett 4:2691–2694

    Article  CAS  Google Scholar 

  94. Fujita K, Fujii T, Yamaguchi R (2004) Org Lett 6:3525–3528

    Article  CAS  Google Scholar 

  95. Bartoszewicz A, Marcos R, Sahoo S, Inge AK, Zou X, Martín-Matute B (2012) Chem Eur J 18:14510–14519

    Article  CAS  Google Scholar 

  96. Yamaguchi R, Kawagoe S, Asai C, Fujita K (2008) Org Lett 10:181–184

    Article  CAS  Google Scholar 

  97. Saidi O, Blacker AJ, Farah MM, Marsdenb SP, Williams JMJ (2010) Chem Commun 46:1541–1543

    Article  CAS  Google Scholar 

  98. Black PJ, Edwards MG, Williams JMJ (2006) Eur J Org Chem 2006:4367–4378

    Article  CAS  Google Scholar 

  99. Black PJ, Cami-Koberi G, Edwards MG, Slatford PA, Whittlesey MK, Williams JMJ (2006) Org Biomol Chem 4:116–125

    Article  CAS  Google Scholar 

  100. Saidi O, Blacker AJ, Lamb GW, Marsden SP, Taylor JE, Williams JMJ (2010) Org Process Res Dev 14:1046–1049

    Article  CAS  Google Scholar 

  101. Blank B, Madalska M, Kempe R (2008) Adv Synth Catal 350:749–758

    Article  CAS  Google Scholar 

  102. Blank B, Michlok S, Kempe R (2009) Chem Eur J 15:3790–3799

    Article  CAS  Google Scholar 

  103. Michlik S, Kempe R (2010) Chem Eur J 16:13193–13198

    Article  CAS  Google Scholar 

  104. Hille T, Irrgang T, Kempe R (2014) Chem Eur J 20:5569–5572

    Article  CAS  Google Scholar 

  105. Cumpstey I, Agrawal S, Borbasa KE, Martín-Matute B (2011) Chem Commun 47:7827–7829

    Article  CAS  Google Scholar 

  106. Agrawal S, Lenormand M, Martín-Matute B (2012) Org Lett 14:1456–1459

    Article  CAS  Google Scholar 

  107. Wang D, Zhao K, Xu C, Miao H, Ding Y (2014) ACS Catal 4:3910–3918

    Article  CAS  Google Scholar 

  108. Wang D, Zhao K, Yu X, Miao H, Ding Y (2014) RSC Adv 4:42924–42929

    Article  CAS  Google Scholar 

  109. Wang D, Zhao K, Ma P, Xu C, Ding Y (2014) Tetrahedron Lett 55:7233–7235

    Article  CAS  Google Scholar 

  110. Li F, Ma J, Wang N (2014) J Org Chem 79:10447–10455

    Article  CAS  Google Scholar 

  111. Jumde VR, Gonsalvi L, Guerriero A, Peruzzini M, Taddei M (2015) Eur J Org Chem 2015:1829–1833

    Article  CAS  Google Scholar 

  112. Yan F, Zhang M, Wang X, Xie F, Chen M (2014) Tetrahedron 70:1193–1198

    Article  CAS  Google Scholar 

  113. Bull ML, Esteruelas MA, Herrero J, Izquiedo S, Pastor IM, Yus M (2013) ACS Catal 3:2072–2075

    Article  CAS  Google Scholar 

  114. Barreiro EJ, Kummerle AE, Fraga CAM (2011) Chem Rev 111:5215–5246

    Article  CAS  Google Scholar 

  115. Schoenherr H, Cernak T (2013) Angew Chem Int Ed 52:12256–12267

    Article  CAS  Google Scholar 

  116. Langhals E, Langhals H (1990) Tetraheron Lett 31:859–862

    Article  CAS  Google Scholar 

  117. Maruoka K, Concepcion AB, Yamamoto H (1994) Synthesis 1994:1283–1290

    Article  Google Scholar 

  118. The Methanol Institute. http://www.methanol.org. Accessed 22 Feb 2016

  119. Cifre PG, Badr O (2007) Energy Convers Manag 48:519–527

    Article  CAS  Google Scholar 

  120. Chang C, Silvestri A (1977) J Catal 47:249–259

    Article  CAS  Google Scholar 

  121. Haw J, Song W, Marcus DM, Nicholas JB (2003) Acc Chem Res 36:317–326

    Article  CAS  Google Scholar 

  122. Ahn JH, Temel B, Iglesia E (2009) Angew Chem Int Ed 48:3814–3816

    Article  CAS  Google Scholar 

  123. Dutta P, Roy SC, Nandi LN, Samuel P, Pillai SM, Bhat BD, Ravindranathan M (2004) J Mol Catal A Chem 223:231–235

    Article  CAS  Google Scholar 

  124. Maitlis PM, Haynes A, Sunley GJ, Howard MJ (1996) J Chem Soc Dalton Trans 11:2187–2196

    Article  Google Scholar 

  125. Thomas CM, Suss-Fink G (2003) Coord Chem Rev 243:125–142

    Article  CAS  Google Scholar 

  126. Haynes A, Maitlis PM, Morris GE, Sunley GJ, Adams H, Badger PW, Bowers CM, Cook DB, Eliott PIP, Ghaffar T, Green H, Griffin TR, Payne M, Pearson JM, Taylor MJ, Vickers PW, Watt RJ (2004) J Am Chem Soc 126:2847–2861

    Article  CAS  Google Scholar 

  127. Qian M, Liauw M, Emig G (2003) Appl Catal A 238:211–222

    Article  CAS  Google Scholar 

  128. Lin W, Chang H (2004) Catal Today 97:181–188

    Article  CAS  Google Scholar 

  129. Yamagata T, Iseki A, Tani K (1997) Chem Lett 12:1215–1216

    Article  Google Scholar 

  130. Tani K, Iseki A, Yamagata T (1999) Chem Commun 18:1821–1833

    Article  Google Scholar 

  131. Rodriguez-Lugo RE, Trincado M, Vogt M, Tewes F, Santiso-uinones G, Grützmacher H (2013) Nat Chem 5:342–347

    Article  CAS  Google Scholar 

  132. Langer R, Fuchs I, Vogt M, Balaraman E, Diskin-Posner Y, Shimon LJW, Ben-David Y, Milstein D (2013) Chem Eur J 19:3407–3414

    Article  CAS  Google Scholar 

  133. Nielsen M, Alberico E, Baumann W, Drexler HJ, Junge H, Gladiali S, Beller M (2013) Nature 495:85–90

    Article  CAS  Google Scholar 

  134. Alberico E, Sponholz P, Cordes C, Nielsen M, Drexler HJ, Baumann W, Junge H, Beller M (2013) Angew Chem Int Ed 52:14162–14166

    Article  CAS  Google Scholar 

  135. Monney A, Barsch E, Sponholz P, Junge H, Ludwig R, Beller M (2014) Chem Commun 50:707–709

    Article  CAS  Google Scholar 

  136. Hu P, Diskin-Posner Y, Ben-David Y, Milstein D (2014) ACS Catal 4:2649–2652

    Article  CAS  Google Scholar 

  137. Dang T, Ramalingam B, Seayad AM (2015) ACS Catal 5:4082–4088

    Article  CAS  Google Scholar 

  138. Moran J, Preetz A, Mesch RA, Krische MJ (2011) Nat Chem 3:287–290

    Article  CAS  Google Scholar 

  139. Li Y, Xue D, Lu W, Wang C, Liu Z, Xiao J (2014) Org Lett 16:66–69

    Article  CAS  Google Scholar 

  140. Sun C, Zou X, Li F (2013) Chem Eur J 19:14030–14033

    Article  CAS  Google Scholar 

  141. Jo E, Lee J, Jun C (2008) Chem Commun 44:5779–5781

    Article  CAS  Google Scholar 

  142. Ortega N, Richer C, Glorius F (2013) Org Lett 15:1776–1779

    Article  CAS  Google Scholar 

  143. Li F, Xie J, Shan H, Sun C, Chen L (2012) RSC Adv 2:8645–8652

    Article  CAS  Google Scholar 

  144. Chan LKM, Poole DL, Shen D, Healy MP, Donohoe TJ (2014) Angew Chem Int Ed 53:761–765

    Article  CAS  Google Scholar 

  145. Ogawa S, Obora Y (2014) Chem Commun 50:2491–2493

    Article  CAS  Google Scholar 

  146. Shen D, Poole DL, Shotton CC, Kornahrens AF, Healy MP, Donohoe TJ (2015) Angew Chem Int Ed 54:1642–1645

    Article  CAS  Google Scholar 

  147. Quan X, Kerdphon S, Andersson PG (2015) Chem Eur J 21:3576–3579

    Article  CAS  Google Scholar 

  148. Li Y, Li H, Junge H, Beller M (2014) Chem Commun 50:14991–14994

    Article  CAS  Google Scholar 

  149. Chen S, Lu G, Cai C (2015) RSC Adv 5:70329–70332

    Article  CAS  Google Scholar 

  150. Li F, Zou X, Wang N (2015) Adv Synth Catal 357:1405–1415

    Article  CAS  Google Scholar 

  151. Grigg R, Mitchell TRB, Sutthivaiyakit S (1981) Tetrahedron Lett 22:4107–4110

    Article  CAS  Google Scholar 

  152. Grigg R, Mitchell TRB, Sutthivaiyakit S, Tongpenyai N (1981) J Chem Soc Chem Commun 12:611–615

    Article  Google Scholar 

  153. Watanabe Y, Tsuji Y, Ohsugi Y (1981) Tetrahedron Lett 22:2667–2670

    Article  CAS  Google Scholar 

  154. Motokura K, Nishimura D, Mori K, Mizugaki T, Ebitani K, Kaneda K (2004) J Am Chem Soc 126:5662–5663

    Article  CAS  Google Scholar 

  155. Löfberg C, Grigg R, Whittaker MA, Keep A, Derrick A (2006) J Org Chem 71:8023–8027

    Article  CAS  Google Scholar 

  156. Motokura K, Fujita N, Mori K, Mizugaki T, Ebitani K, Jitsukawa K, Kaneda K (2006) Chem Eur J 12:8228–8239

    Article  CAS  Google Scholar 

  157. Cheung H, Li J, Zheng W, Zhou Z, Chiu Y, Lin Z, Lau C (2010) Dalton Trans 39:265–274

    Article  CAS  Google Scholar 

  158. Grigg R, Löfberg C, Whitney S, Sridharan V, Keep A, Derrick A (2009) Tetrahedron 65:849–854

    Article  CAS  Google Scholar 

  159. Cho CS, Kim BT, Kim TJ, Shim SC (2001) J Org Chem 66:9020–9022

    Article  CAS  Google Scholar 

  160. Onodera G, Nishibayashi Y, Uemura S (2006) Angew Chem Int Ed 45:3819–3822

    Article  CAS  Google Scholar 

  161. Morita M, Obora Y, Ishii Y (2007) Chem Commun 27:2850–2852

    Article  Google Scholar 

  162. Iuchi Y, Hyotanishi M, Miller BE, Maeda K, Obora Y, Ishii Y (2010) J Org Chem 75:1803–1806

    Article  CAS  Google Scholar 

  163. Weissermel K, Arpe HJ (eds) (2010) Industrial organic chemistry, 5th edn. Wiley-VCH, Weinheim

    Google Scholar 

  164. Anxionnat B, Gomez Pardo D, Ricci G, Cossy J (2011) J Org Lett 13:4084–4087

    Article  CAS  Google Scholar 

  165. Sawaguchi T, Obora Y (2011) Chem Lett 40:1055–1057

    Article  CAS  Google Scholar 

  166. Kuwahara T, Fukuyama T, Ryu I (2013) Chem Lett 42:1163–1165

    Article  CAS  Google Scholar 

  167. Guo L, Lin Y, Yao W, Leng X, Huang Z (2013) Org Lett 15:1144–1147

    Article  CAS  Google Scholar 

  168. Kuwahara T, Fukuyama Y, Ryu I (2013) RSC Adv 3:13702–13704

    Article  CAS  Google Scholar 

  169. Zakarian A, Batch A, Holton RA (2003) J Am Chem Soc 125:7822–7824

    Article  CAS  Google Scholar 

  170. Danishefsky S, Vaughan K, Gadwood R, Tsuzuki K (1981) J Am Chem Soc 103:4136–4141

    Article  CAS  Google Scholar 

  171. Ling T, Chowdhury C, Kramer BA, Vong BG, Palladino MA, Theodorakis A (2001) J Org Chem 66:8843–8853

    Article  CAS  Google Scholar 

  172. Iuchi Y, Obora Y, Ishii Y (2010) J Am Chem Soc 132:2536–2537

    Article  CAS  Google Scholar 

  173. Guo L, Ma X, Fang H, Jia X, Huang Z (2015) Angew Chem Int Ed 54:4023–4027

    Article  CAS  Google Scholar 

  174. Blank B, Kempe R (2010) J Am Chem Soc 132:924–925

    Article  CAS  Google Scholar 

  175. Obora Y, Ogawa S, Yamamoto N (2012) J Org Chem 77:9429–9433

    Article  CAS  Google Scholar 

  176. Chaudhari C, Siddiki SMAH, Shimizu K (2013) Tetrahedron Lett 54:6490–6493

    Article  CAS  Google Scholar 

  177. Nandakumar A, Midya SP, Landge VG, Balaraman E (2015) Angew Chem Int Ed 54:11022–11034

    Article  CAS  Google Scholar 

  178. Xiong B, Li Y, Lv W, Tan Z, Jiang H, Zhang M (2015) Org Lett 17:4054–4057

    Article  CAS  Google Scholar 

  179. Waykole C, Bhowmick D, Pratap A (2014) J Am Oil Chem Soc 91:1407–1416

    Article  CAS  Google Scholar 

  180. Xu G, Lammens T, Liu Q, Wang X, Dong L, Caiazzo A, Ashraf N, Guan J, Mu X (2014) Green Chem 16:3971–3977

    Article  CAS  Google Scholar 

  181. Silvester L, Lamonier JF, Faye J, Capron M, Vanner RN, Lamoniew C, Dubois JL, Coururier JL, Calais C, Dumeignil F (2015) Cat Sci Technol 5:2994–3006

    Article  CAS  Google Scholar 

  182. Kozlowski JT, Davis RJ (2013) ACS Catal 3:1588–1600

    Article  CAS  Google Scholar 

  183. Cano R, Yus M, Ramón DJ (2012) Chem Commun 48:7628–7630

    Article  CAS  Google Scholar 

  184. Bai W, Jia G (2015) Inorg Chim Acta 431:234–241

    Article  CAS  Google Scholar 

  185. Dowson GRM, Haddow MF, Lee J, Wingad RL, Wass DF (2013) Angew Chem Int Ed 52:9005–9008

    Article  CAS  Google Scholar 

  186. Zhang X, Lin Z, Xu X, Yue H, Tian G, Feng S (2013) ACS Sustain Chem Eng 1:1493–1497

    Article  CAS  Google Scholar 

  187. Obora Y, Anno Y, Okamoto R, Matsu-ura T, Ishii Y (2011) Angew Chem Int Ed 50:8618–8622

    Article  CAS  Google Scholar 

  188. Ikeda T, Lee B, Kurihara S, Tazuke S, Ito S, Yamamoto M (1988) J Am Chem Soc 110:8299–8304

    Article  CAS  Google Scholar 

  189. Wang J, Doubleday C Jr, Turro NJ (1989) J Am Chem Soc 111:3962–3965

    Article  CAS  Google Scholar 

  190. Yamaji M, Tsukada H, Nishimura J, Shizuka H, Tobita S (2002) Chem Phys Lett 357:137–142

    Article  CAS  Google Scholar 

  191. Tani K, Tohda Y, Takemura H, Ohkita H, Ito S, Yamamoto M (2001) Chem Commun 19:1914–1915

    Article  CAS  Google Scholar 

  192. Makarov IS, Madsen R (2013) J Org Chem 78:6593–6598

    Article  CAS  Google Scholar 

  193. Mura MG, De Luca L, Taddei M, Williams JAM, Porcheddu A (2014) Org Lett 16:2586–2589

    Article  CAS  Google Scholar 

  194. Shimizu K (2015) Cat Sci Technol 5:1412–1427

    Article  CAS  Google Scholar 

  195. Shan SP, Tuan DT, Seayad AM, Ramalingam B (2014) ChemCatChem 6:808–814

    Article  CAS  Google Scholar 

  196. Peeters A, Claes L, Geukens I, Stassen I, De Vos D (2014) Appl Catal A 469:191–197

    Article  CAS  Google Scholar 

  197. Yamaguchi K, He J, Oishi T, Mizuno N (2010) Chem Eur J 16:7199–7207

    Article  CAS  Google Scholar 

  198. Rasero-Almansa AM, Corma A, Iglesias M, Sanchez F (2014) ChemCatChem 6:1794–1800

    Article  CAS  Google Scholar 

  199. Wang D, Guo X, Wang C, Wang Y, Zhong R, Zhu X, Cai L, Gao Z, Hou X (2013) Adv Synth Catal 355:1117–1125

    Article  CAS  Google Scholar 

  200. Corma A, Navas J, Sabater MJ (2012) Chem Eur J 18:14150–14156

    Article  CAS  Google Scholar 

  201. He L, Qian Y, Ding R, Liu Y, He H, Fan K, Cao Y (2012) ChemSusChem 5:621–624

    Article  CAS  Google Scholar 

  202. Ishida T, Takamura R, Takei T, Akita T, Haruta M (2012) Appl Catal A 413–414:261–266

    Article  CAS  Google Scholar 

  203. Tang C, He L, Liu Y, Cao Y, He H, Fan K (2011) Chem Eur J 17:7172–7177

    Article  CAS  Google Scholar 

  204. He L, Lou X, Ni J, Liu Y, Cao Y, He H, Fan K (2010) Chem Eur J 16:13965–13969

    Article  CAS  Google Scholar 

  205. Liu H, Chuah G, Jaenicke S (2012) J Catal 292:130–137

    Article  CAS  Google Scholar 

  206. Shimizu K, Shimura K, Nishimura M, Satsuma A (2011) ChemCatChem 3:1755–1758

    Article  CAS  Google Scholar 

  207. Shimizu K, Nishimura M, Satsuma A (2009) ChemCatChem 1:497–503

    Article  CAS  Google Scholar 

  208. Cano R, Yus M, Ramon DJ (2011) Tetrahedron 67:8079–8085

    Article  CAS  Google Scholar 

  209. Zhang Y, Qi X, Cui X, Shi F, Deng Y (2011) Tetrahedron Lett 52:1334–1338

    Article  CAS  Google Scholar 

  210. Shirasaki Y, Fujiwara K, Sugano Y, Ichikawa S, Hirai T (2013) ACS Catal 3:312–320

    Article  CAS  Google Scholar 

  211. Ousmane M, Perrussel G, Yan Z, Clacens JM, De Campo F, Pera-Titus M (2014) J Catal 309:439–452

    Article  CAS  Google Scholar 

  212. Corma A, Rodenas T, Sabater MJ (2010) Chem Eur J 16:254–260

    Article  CAS  Google Scholar 

  213. Mehta A, Thakev A, Londhe V, Nandan SR (2014) Appl Catal A 478:241–251

    Article  CAS  Google Scholar 

  214. Shimizu K, Imaiida N, Kon K, Siddiki SMAH, Satsuma A (2013) ACS Catal 3:998–1005

    Article  CAS  Google Scholar 

  215. Ueno S, Usui K, Kuwano K (2011) Synlett 2011:1303–1307

    Article  CAS  Google Scholar 

  216. Santoro F, Psaro R, Ravasio N, Zaccheria F (2014) RSC Adv 4:2596–2600

    Article  CAS  Google Scholar 

  217. Dixit M, Mishra M, Joshi PA, Shah DO (2013) Catal Commun 33:80–83

    Article  CAS  Google Scholar 

  218. Santoro F, Psaro R, Ravasio N, Zaccheria F (2012) ChemCatChem 4:1249–1254

    Article  CAS  Google Scholar 

  219. Perez JM, Cano R, Yus M, Ramon DJ (2012) Eur J Org Chem 2012:4548–4554

    Article  CAS  Google Scholar 

  220. He J, Yamaguchi K, Mizuno N (2010) Chem Lett 39:1182–1183

    Article  CAS  Google Scholar 

  221. Likhar PR, Arundhathi R et al (2009) Eur J Org Chem 2009:5383–5389

    Article  CAS  Google Scholar 

  222. Gonzalez-Arellano C, Yoshida K, Luque R, Gai PL (2010) Green Chem 12:1281–1287

    Article  CAS  Google Scholar 

  223. Yu X, Liu C, Jiang L, Xu Q (2011) Org Lett 13:6184–6187

    Article  CAS  Google Scholar 

  224. Dang T, Shan S, Ramalingam B, Seayad AM (2015) RSC Adv 5:42399–42406

    Article  CAS  Google Scholar 

  225. Culkin DA, Hartwig JF (2003) Acc Chem Res 36:234–245

    Article  CAS  Google Scholar 

  226. Bellina F, Rossi R (2010) Chem Rev 110:1082–1146

    Article  CAS  Google Scholar 

  227. Li C (2009) Acc Chem Res 42:335–344

    Article  CAS  Google Scholar 

  228. Campos KR (2007) Chem Soc Rev 36:1069–1084

    Article  CAS  Google Scholar 

  229. Li H, Li J, Shi Z (2011) Catal Sci Technol 1:191–206

    Article  CAS  Google Scholar 

  230. Fox JM, Huang X, Chieffi A, Buchwald SL (2000) J Am Chem Soc 122:1360–1370

    Article  CAS  Google Scholar 

  231. Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W (2008) Organometallics 27:1679–1682

    Article  CAS  Google Scholar 

  232. Nguyen HN, Huang X, Buchwald SL (2003) J Am Chem Soc 125:11818–11819

    Article  CAS  Google Scholar 

  233. Liao X, Weng Z, Hartwig JF (2008) J Am Chem Soc 130:195–200

    Article  CAS  Google Scholar 

  234. Li B, Darcel C, Dixneuf PH (2014) Chem Commun 50:5970–5972

    Article  CAS  Google Scholar 

  235. Labed A, Jiang F, Labed I, Lator A, Peters M, Achard M, Kabouche A, Kabouche Z, Sharma GVM, Bruneau C (2015) ChemCatChem 7:1090–1096

    Article  CAS  Google Scholar 

  236. Allen LJ, Crabtree RH (2010) Green Chem 12:1362–1364

    Article  CAS  Google Scholar 

  237. Xu Q, Chen J, Tian H, Yuan X, Li S, Zhou C, Liu J (2014) Angew Chem Int Ed 53:225–229

    Article  CAS  Google Scholar 

  238. Liang Y, Zhou X, Tang S, Huang Y, Feng Y, Xu H (2013) RSC Adv 3:7739–7742

    Article  CAS  Google Scholar 

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Obora, Y. C-Alkylation by Hydrogen Autotransfer Reactions. Top Curr Chem (Z) 374, 11 (2016). https://doi.org/10.1007/s41061-016-0012-8

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