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Reactions of Pyridines, Benzopyridines, and Azapyridines with Organomagnesiums and Organolithiums

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Metalation of Azines and Diazines

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 31))

Abstract

A survey is given on how simple pyridines can be elaborated into substituted and functionalized structures based on organometallic chemistry. “Organometallics” in the given context means “polar” reagents, i.e. those containing organoalkali or organoalkaline-earth metals, in particular, organolithiums and organomagnesiums. For comparison, non-organometallic methods are summarized at the beginning and transition-metal chemistry at the very end. The review is critical. Emphasis is placed on the practicability and superiority of a method; novelty alone is not a sufficient criterion for coverage.

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Abbreviations

Ar:

Argon

BOC:

tert-Butoxycarbonyl

DABCO:

1,8-Diazabicyclo[2.2.2]octane

DEE:

Diethyl ether

El :

Electrophilic part of a reagent El-X

El-X:

Electrophilic reagent

HEX:

Hexanes (or petroleum ether of bp ~65°C)

LIC-KOR:

Superbasic 1:1 mixture of n-butyllithium and potassium tert-butoxide

LIDA:

Lithium diisopropylamide

LIDMAE:

Lithium 2-(dimethylamino)ethoxide

LIM-KOR:

Superbasic 1:1 mixture of methyllithium and potassium tert-butoxide

LIPIP:

Lithium piperid-1-ide (N-piperidyllithium)

LIS-KOR:

Superbasic 1:1 mixture of sec-butyllithium and potassium tert-butoxide

LIT-KOR:

Superbasic 1:1 mixture of tert-butyllithium and potassium tert-butoxide

LITMP:

Lithium 2,2,6,6-tetramethylpiperid-1-ide (tetramethylpiperid-1-yllithium)

M-Nu :

Nucleophilic reagent (M = metal, e.g., Li)

Nu :

An amine or the nucleophilic part of a reagent

PMDTA:

N,N,N′,N″,N″-pentamethyldiethylenetriamine

R:

Alkyl or Aryl

spec.:

Specifically (on this or that page)

Sv :

Solvent

THF:

Tetrahydrofuran

TMEDA:

N,N'-tetramethylethylenediamine

+25°C:

Ambient temperature (in general between 23°C and 26°C)

−75°C:

Average temperature of dry ice/solvent baths

n-LiC4H9 :

The Old-German n-alkyl is perhaps the only unforgiveable sin one can commit against modern nomenclature. However, one does not find any butyllithium in the catalogs of chemicals suppliers, just n- or sec- or tert-butyllithium. To avoid confusion among our readers, we also specify n-butyllithium whenever appropriate. This violation of rules is of course not extended to any other compound, be it butyl chloride or hexyllithium.

inert gas:

Reactions performed on a small scale (<25 mmol) may be run under an atmosphere of 99.999% pure nitrogen to minimize losses caused by moisture or oxygen. Such protection is not required for preparative scale reactions unless they last many hours.

References

  1. Abramovitch RA (ed) (1974–1975) The chemistry of heterocyclic compounds: pyridines and its derivatives, vol. 14, supplements part 1–4. Wiley, New York

    Google Scholar 

  2. Newkome GR (ed) (1984) The chemistry of heterocyclic compounds: pyridines and its derivatives, vol. 14, supplement part 5. Wiley, New York

    Google Scholar 

  3. Joule JA, Mills K, Smith GF (1998) Heterocyclic chemistry, 3rd edn. Stanley Thornes, Cheltenham

    Google Scholar 

  4. Joule JA, Mills K (2000) Heterocyclic chemistry, 4th edn. Blackwell, Oxford

    Google Scholar 

  5. Spitzner D (1991) Houben-Weyl: methods of organic synthesis, vol E7. Thieme, Stuttgart

    Google Scholar 

  6. Spitzner D (2005) Science of synthesis, vol 15. Thieme, Stuttgart

    Google Scholar 

  7. Wang Y, Wu JI-C, Li Q, Schleyer PVR (2010) Org Lett 12:4824–4827

    CAS  Google Scholar 

  8. Clark RD, Jahangir A (1995) Org React 47:1–314

    CAS  Google Scholar 

  9. Itami K, Kamei T, Mitsudo K, Nokami T, Yoshida J-i (2001) J Org Chem 66:3970–3976

    CAS  Google Scholar 

  10. Fontana F, Minisci F, Nogueira Barbosa MC, Vismara E (1990) Tetrahedron 46:2525–2538

    CAS  Google Scholar 

  11. Minisci FV, Vismara E, Fontana F (1989) Heterocycles 28:489–519

    CAS  Google Scholar 

  12. Schlosser M (2002) in: Schlosser M (ed) Organometallics in synthesis: 2nd manual. Wiley, Chichester, pp 1–352 (spec. 73–81)

    Google Scholar 

  13. Eisch JJ, Russo DA (1968) J Organomet Chem 14:P13–P16

    CAS  Google Scholar 

  14. Clarke AJ, McNamara S, Meth-Cohn O (1974) Tetrahedron Lett 15:2373–2376

    Google Scholar 

  15. Ward RL (1961) J Am Chem Soc 83:3623–3626

    CAS  Google Scholar 

  16. Schmulbach CD, Hinckley CC, Wasmund D (1968) J Am Chem Soc 90:6600–6602

    CAS  Google Scholar 

  17. Comins DL, O’Connor S (1988) Adv Heterocycl Chem 44:199–267

    CAS  Google Scholar 

  18. Olah GA, Olah JA, Overchuk NA (1965) J Org Chem 30:3373–3376

    CAS  Google Scholar 

  19. Katritzky AR, Fan W-Q (1992) Heterocycles 34:2179–2229

    Google Scholar 

  20. Räth C (1931) Liebigs Ann Chem 486:95–106

    Google Scholar 

  21. Bakke JM, Hegbom I, Øvereeide E, Aaby K (1994) Acta Chem Scand 48:1001–1006

    CAS  Google Scholar 

  22. Bakke JM (2003) Pure Appl Chem 75:1403–1415

    CAS  Google Scholar 

  23. Katritzky AR, Scriven EFV, Majumder S, Akhmedova RG, Vakulenko AV, Akhmedov NG, Murugan R, Abboud KA (2005) Org Biomol Chem 3:538–541

    CAS  Google Scholar 

  24. den Hertog HJ, Wibaut JP (1932) Recl Trav Chim Pays-Bas 51:381–388

    CAS  Google Scholar 

  25. den Hertog HJ, van der Does L, Landheer CA (1962) Recl Trav Chim Pays-Bas 81:864–870

    Google Scholar 

  26. Kirpal A, Reiter E (1925) Ber Dtsch Chem Ges 58:699–701

    Google Scholar 

  27. den Hertog HJ, Overhoff J (1930) Recl Trav Chim Pays-Bas 49:552–556

    Google Scholar 

  28. den Hertog HJ, Overhoff J (1950) Recl Trav Chim Pays-Bas 69:468–473

    Google Scholar 

  29. Kirpal A, Böhm W (1932) Ber Dtsch Chem Ges 65:680–682

    Google Scholar 

  30. Fox GJ, Hepworth JD, Hallas G (1973) J Chem Soc Perkin Trans 1:68–69

    Google Scholar 

  31. Dolci L (1999) Bioorg Med Chem 7:467–480

    CAS  Google Scholar 

  32. den Hertog HJ (1945) Recl Trav Chim Pays-Bas 64:85–101

    Google Scholar 

  33. Wibaut JP, den Hertog HJ (1945) Recl Trav Chim Pays-Bas 64:55–64

    CAS  Google Scholar 

  34. Wibaut JP, Nicolai JR (1939) Recl Trav Chim Pays-Bas 58:709–721

    CAS  Google Scholar 

  35. Cañibano V, Rodríguez JF, Santos M, Sanz-Tejedor MA, Careño MC, Gonzáles G, García-Ruano JL (2001) Synthesis 2175–2179

    Google Scholar 

  36. Tschitschibabin A (1915) Chem Zbl 86I:1066

    Google Scholar 

  37. Płaźek E, Sucharda E (1928) Ber Dtsch Chem Ges 61

    Google Scholar 

  38. Paudler WW, Jovanovic MC (1983) J Org Chem 48:1064–1069

    CAS  Google Scholar 

  39. den Hertog HJ, Jouwersma C (1953) Recl Trav Chim Pays-Bas 72:125–134

    Google Scholar 

  40. Bakke JM, Riha J (1999) J Heterocycl Chem 36:1143–1146

    CAS  Google Scholar 

  41. Antoine M, Czech M, Gerlach M, Günther E, Schuster T, Marchand P (2011) Synthesis 794–806

    Google Scholar 

  42. Cañibano V, Rodriguez JF, Santos M, Sanz-Tejedor MA, Ascensión M, Carreño MC, Gonzáles G, Garcia-Ruano JL (2001) Synthesis 2175–2179

    Google Scholar 

  43. Van Der Puy M, Nalwajek D, Wicks GE (1988) Tetrahedron Lett 29:4389–4392

    Google Scholar 

  44. Quarroz D (1984) Swiss Patent 644 847 A5 19840831 (to Lonza)

    Google Scholar 

  45. Quarroz D (1983) Eur Patent Appl EP 84118 A1 19830727 (to Lonza)

    Google Scholar 

  46. Quarroz D (1983) Eur Pat Appl EP 90173 A1 19831005 (to Lonza)

    Google Scholar 

  47. Umemoto T, Tomizawa G (1987) Tetrahedron Lett 28:2705–2708

    CAS  Google Scholar 

  48. Prill EA, McElvain SM (1943) Org Synth Coll 2:419–421

    Google Scholar 

  49. Tschitschibabin A, Seide O (1915) Chem Zbl 86I:1064–1065

    Google Scholar 

  50. Vorbrüggen H (1990) Adv Heterocycl Chem 49:117–192

    Google Scholar 

  51. Rykowski A, van der Plas HC (1985) Synthesis 884–886

    Google Scholar 

  52. Zoltewicz JA, Helmick LS, Oestreich TM, King RW, Kandetzki PE (1973) J Org Chem 38:1947–1949

    CAS  Google Scholar 

  53. Woźniak M, Baránski A, Nowak K, van der Plas HC (1987) J Org Chem 52:5643–5646

    Google Scholar 

  54. Fife WK, Scriven EFV (1984) Heterocycles 22:2375–2394

    CAS  Google Scholar 

  55. Popp FD, Takeuchi I, Kant J, Hamada Y (1987) Chem Commun 1765–1766

    Google Scholar 

  56. Kant J, Popp FD (1985) Chem Ind (Lond) 125–126

    Google Scholar 

  57. Duarte FF, Popp FD, Holder AJ (1993) J Heterocycl Chem 30:893–896

    CAS  Google Scholar 

  58. Popp FD, Uff BC (1985) Heterocycles 23:731–740

    CAS  Google Scholar 

  59. Schlosser M, Cottet F (2002) Eur J Org Chem 4181–4184

    Google Scholar 

  60. Fukuhara T, Yoneda N (1993) Chem Lett 509–512

    Google Scholar 

  61. Bobbio C, Rausis T, Schlosser M (2005) Chem Eur J 11:1903–1910

    CAS  Google Scholar 

  62. den Hertog HJ, Schogt JCM, de Bruyn J, de Klerk A (1950) Recl Trav Chim Pays-Bas 69:673–699

    Google Scholar 

  63. Parks EL, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) Tetrahedron 66:6195–6204

    CAS  Google Scholar 

  64. Sakamoto T, Kaneda S-I, Nishimura S, Yamanaka H (1985) Chem Pharm Bull 33:565–571

    CAS  Google Scholar 

  65. Schlosser M, Bobbio C, Rausis T (2005) J Org Chem 70:2494–2502

    CAS  Google Scholar 

  66. Schlosser M, Ruzziconi R (2010) Synthesis 2111–2123

    Google Scholar 

  67. Marckwald W (1894) Ber Dtsch Chem Ges 27:1317–1346 (spec. 1323)

    Google Scholar 

  68. Tschitschibabin AE, Tyazhelova VS (1923) Chem Zbl 94III:1021

    Google Scholar 

  69. Craig LC (1934) J Am Chem Soc 56:231–232

    CAS  Google Scholar 

  70. Allen CFH, Thirtle JR (1955) Org Synth Coll 3:136–138

    Google Scholar 

  71. Kondo S, Nakanishi M, Tsuda K (1984) J Heterocycl Chem 21:1243–1244

    CAS  Google Scholar 

  72. Graf R, Lederek-Ponzer E, Freiberg L (1931) Ber Dtsch Chem Ges 64:21–26

    Google Scholar 

  73. Tschitschibabin AE, Jegorow A (1928) Chem Zbl 99II:1670–1671

    Google Scholar 

  74. Case FH (1946) J Am Chem Soc 68:2574–2577

    CAS  Google Scholar 

  75. Baik W, Luan W, Lee HJ, Yoon CH, Sangho K, Kim BH (2005) Can J Chem 83:213–219

    CAS  Google Scholar 

  76. Talik T, Talik Z (1964) Tetrahedron (suppl 6):81–88

    Google Scholar 

  77. Balz G, Schiemann G (1927) Ber Dtsch Chem Ges 60:1186–1190

    Google Scholar 

  78. Hand ES, Baker DC (1989) Synthesis 905–908

    Google Scholar 

  79. Osswald P, Scherer O (1933) DR Pat 600 706 (to IG Farben)

    Google Scholar 

  80. Yoneda N, Fukuhara T (1996) Tetrahedron 52:23–26

    CAS  Google Scholar 

  81. Wibaut J-P, Holmes-Kamminga WJ (1958) Bull Soc Chim Fr 424–428

    Google Scholar 

  82. Roe A (1949) Org React 5:193–228

    CAS  Google Scholar 

  83. Rutherford KG, Redmond W (1973) Org Synth Coll 5:133–136

    Google Scholar 

  84. Camps R (1902) Arch Pharm (Weinheim) 240:345–365 (spec. 358)

    CAS  Google Scholar 

  85. Zwart C, Wibaut JP (1955) Recl Trav Chim Pays-Bas 74:1062–1069

    CAS  Google Scholar 

  86. Schmidt-Thome J, Göbel H (1951) Hoppe-Seylers Z Physiol Chem 288:237–243

    CAS  Google Scholar 

  87. Kijima A, Sekiguchi S (1987) Bull Chem Soc Jpn 60:3597–3602

    CAS  Google Scholar 

  88. Dimroth P, Radtke V (1979) Liebigs Ann Chem 769–775

    Google Scholar 

  89. Sugimoto O, Mori M, Moriya K, Tanji K-i (2001) Helv Chim Acta 84:1112–1118

    CAS  Google Scholar 

  90. Sun Z, Wang H, Wen K, Fan E (2011) J Org Chem 76:4149–4153

    CAS  Google Scholar 

  91. Garcia-Lago R, Alonso-Gómez JL, Sicre C, Cid M-M (2008) Heterocycles 75:57–64

    CAS  Google Scholar 

  92. Iddon B, Mack AG, Suschitzky H, Taylor JA, Wakefield BJ (1980) J Chem Soc Perkin Trans 1:1370–1380

    Google Scholar 

  93. den Hertog HJ, De Bruyn J (1951) Recl Trav Chim Pays-Bas 70:182–190

    Google Scholar 

  94. Binz A, Schickh O (1935) Ber Dtsch Chem Ges 68:315–324

    Google Scholar 

  95. Bobrański B, Kochańska L, Kowalewska A (1938) Ber Dtsch Chem Ges 71:2385–2388

    Google Scholar 

  96. den Hertog HJ, Maas J, Kolder CR, Combe WP (1955) Recl Trav Chim Pays-Bas 74:59–68

    Google Scholar 

  97. Yamanaka H, Araki T, Sakamoto T (1988) Chem Pharm Bull 36:2244–2247

    CAS  Google Scholar 

  98. Dehmlow EV, Schulz H-J (1985) Tetrahedron Lett 26:4903–4906

    CAS  Google Scholar 

  99. Kolder CR, Den Hertog HJ (1953) Recl Trav Chim Pays-Bas 72:285–295

    CAS  Google Scholar 

  100. Schickh v O, Binz A, Schulz A (1936) Ber Dtsch Chem Ges 69:2593–2605

    Google Scholar 

  101. Malinowski M, Kaszmarek L (1987) Synthesis 1013–1015

    Google Scholar 

  102. Tschitschibabin AE, Kirsonow AW (1927) Ber Dtsch Chem Ges 60:766–776 (spec. 775)

    Google Scholar 

  103. Balicki R, Maciejewski C (2002) Synth Commun 32:1681–1683

    CAS  Google Scholar 

  104. Kasparian AJ, Sacvarin C, Allgeier AM, Walker SD (2011) J Org Chem 76:9841–9844

    CAS  Google Scholar 

  105. Bera MK, Hommes P, Reissig H-U (2011) Chem Eur J 17:11838–11843

    CAS  Google Scholar 

  106. Stout DM, Meyers AI (1982) Chem Rev 82:223–243

    CAS  Google Scholar 

  107. Birch AJ, Karakhanov EA (1975) Chem Commun 480–481

    Google Scholar 

  108. Schneider P (1979) Doctoral Dissertation. Ecole Polytechnique Fédérale Lausanne, pp 55–56

    Google Scholar 

  109. de Koning AJ, Budzelaar PHM, Brandsma L, de Bie MJA, Boersma J (1980) Tetrahedron Lett 21:2105–2108

    Google Scholar 

  110. Ferles M (1958) Collect Czech Chem Commun 23:479–484

    Google Scholar 

  111. Ferles M, Attia A, Šilhánková A (1973) Collect Czech Chem Commun 38:615–619

    CAS  Google Scholar 

  112. Anderson PS, Kruger WE, Lyle RE (1965) Tetrahedron Lett 6:4011–4017

    Google Scholar 

  113. Holik M, Ferles M (1965) Collect Czech Chem Commun 30:3067–3070

    Google Scholar 

  114. Biellmann JF, Callot HJ (1968) Bull Soc Chim Fr 1154–1159

    Google Scholar 

  115. Biellmann JF, Callot HJ (1968) Bull Soc Chim Fr 1159–1165

    Google Scholar 

  116. Chambers RD, Iddon B, Musgrave WKR (1964) J Chem Soc 3736–3739

    Google Scholar 

  117. Banks RE, Burgess JE, Cheng WM, Haszeldine RN (1968) J Chem Soc 575–581

    Google Scholar 

  118. Chambers RD, Iddon B, Musgrave WKR, Chadwick L (1968) Tetrahedron 24:877–885

    CAS  Google Scholar 

  119. Matsumoto K, Kannami M, Oda M (2003) Tetrahedron Lett 44:2861–2864

    CAS  Google Scholar 

  120. Uenishi J, Tanaka T, Wakabayashi S, Oae S, Tsukube H (1990) Tetrahedron Lett 31:4625–4628

    CAS  Google Scholar 

  121. McKenzie TC, Glass D (1987) J Heterocycl Chem 24:1551–1553

    CAS  Google Scholar 

  122. Ziegler K, Zeiser K (1930) Ber Dtsch Chem Ges 63:1847–1851

    Google Scholar 

  123. Ziegler K, Zeiser K (1931) Liebigs Ann Chem 485:174–192

    CAS  Google Scholar 

  124. Francis RF, Davis W, Wisener JT (1974) J Org Chem 39:59–62

    CAS  Google Scholar 

  125. Mazzanti A, Lunazzi L, Lepri S, Ruzziconi R, Schlosser M (2011) Eur J Org Chem 6725–6731

    Google Scholar 

  126. Harden DB, Mokrosz MJ, Strekowski L (1988) J Org Chem 53:4137–4140

    CAS  Google Scholar 

  127. Bursavitch MG, Lombardi S, Gilbert AM (2005) Org Lett 7:4113–4116

    Google Scholar 

  128. Nakamura H, Aizawa M, Murai A (1996) Synlett 1015–1016

    Google Scholar 

  129. Veer WLC, Goldschmidt S (1946) Recl Trav Chim Pays-Bas 65:793–795

    CAS  Google Scholar 

  130. Iida T, Wada T, Tomimoto K, Mase T (2001) Tetrahedron Lett 42:4841–4844

    CAS  Google Scholar 

  131. Inoue A, Kitagawa K, Shinokubo H, Oshima K (2001) J Org Chem 66:4333–4339

    CAS  Google Scholar 

  132. Ackermann L (2009) Chem Uns Zeit 43:74–83

    CAS  Google Scholar 

  133. Cook NC, Lyons JE (1966) J Am Chem Soc 88:3396–3403

    CAS  Google Scholar 

  134. Giam CS, Knaus EE, Pasutto FM (1974) J Org Chem 39:3565–3568

    CAS  Google Scholar 

  135. Giam CS, Stout JL (1970) Chem Commun 478–478

    Google Scholar 

  136. Giam CS, Knaus EE, Lockhart RA, Keener IG (1975) Can J Chem 53:2305–2310

    CAS  Google Scholar 

  137. Klemm LH, Burel W, Purtzer D (1992) J Heterocycl Chem 29:1673–1675

    CAS  Google Scholar 

  138. Doyle P, Yates RRJ (1970) Tetrahedron Lett 11:3371–3374

    Google Scholar 

  139. Finch N, Gemenden CW (1975) J Org Chem 40:569–574

    CAS  Google Scholar 

  140. Zhang L-H, Tan Z (2000) Tetrahedron Lett 41:3025–3028

    CAS  Google Scholar 

  141. Boesvel WM, Hitchcock PB, Lappert MF (1997) Chem Commun 2091–2092

    Google Scholar 

  142. Sliwa W (1992) N-substituted salts of pyridines. Springer, Berlin

    Google Scholar 

  143. Thiessen LM, Lepoivre JA, Alderweireldt FC (1974) Tetrahedron Lett 15:59–62

    Google Scholar 

  144. Wang X, Kauppi AM, Olsson R, Almquist F (2003) Eur J Org Chem 4586–4592

    Google Scholar 

  145. Charette AB, Grenon M, Lemire A, Pourashraf M, Martel J (2001) J Am Chem Soc 123:11829–11830

    CAS  Google Scholar 

  146. Abramovitch RA, Smith EM, Knaus EE, Saha M (1972) J Org Chem 37:1690–1696

    CAS  Google Scholar 

  147. Abramovitch RA, Coutts RT, Smith EM (1972) J Org Chem 37:3584–3587

    CAS  Google Scholar 

  148. Colonna M, Risaliti A (1953) Gazz Chim Ital 83:58–61

    CAS  Google Scholar 

  149. Kato T, Yamanaka H (1965) J Org Chem 30:910–930

    CAS  Google Scholar 

  150. Andersson H, Banchelin TS-L, Das S, Olsson R, Almquist F (2010) Chem Commun 3384–3386

    Google Scholar 

  151. Andersson H, Olsson R, Almquist F (2011) Org Biomol Chem 9:337–346

    CAS  Google Scholar 

  152. Kellogg RM, van Bergen TJ (1971) J Org Chem 36:1705–1708

    CAS  Google Scholar 

  153. Tagawa Y, Nomura M, Yamashita H, Goto Y, Hamana M (1999) Heterocycles 51:2385–2398

    CAS  Google Scholar 

  154. Schiess P, Ringele P (1972) Tetrahedron Lett 13:311–312

    Google Scholar 

  155. Fritzsche U, Hünig S (1974) Liebigs Ann Chem 1407–1414

    Google Scholar 

  156. Eisenthal R, Katritzky AR (1965) Tetrahedron 21:2205–2213

    CAS  Google Scholar 

  157. Al-Arnaoult A, Courtois G, Miginiac L (1987) J Organomet Chem 333:139–153

    Google Scholar 

  158. Becher J (1980) Synthesis 589–612

    Google Scholar 

  159. Becher J (1988) Org Synth Coll 6:640–644

    Google Scholar 

  160. Bakke JM, Ranes E, Riha J (1998) Tetrahedron Lett 39:911–912

    CAS  Google Scholar 

  161. Wittig G, Harborth G (1944) Ber Dtsch Chem Ges 77:315–325 (spec. 322)

    Google Scholar 

  162. Gilman H, Haubein AH (1944) J Am Chem Soc 66:1515–1516

    CAS  Google Scholar 

  163. Parham WE, Piccirilli RM (1977) J Org Chem 42:257–260

    CAS  Google Scholar 

  164. Wang X, Rabbat P, O’Shea P, Tillyer R, Grabowski EJJ, Reider PJ (2000) Tetrahedron Lett 41:4335–4338

    CAS  Google Scholar 

  165. Mallet M, Quéguiner G (1979) Tetrahedron 35:1625–1631

    CAS  Google Scholar 

  166. Bobbio C, Schlosser M (2002), unpublished results

    Google Scholar 

  167. Schlosser M, Guio L, Leroux F (2001) J Am Chem Soc 123:3822–3823

    CAS  Google Scholar 

  168. Gribble GW, Saulnier MG (1980) Tetrahedron Lett 21:4137–4140

    CAS  Google Scholar 

  169. Gribble GW, Saulnier MG (1993) Heterocycles 35:151–169

    CAS  Google Scholar 

  170. Chan ASC, Chen C-C, Cao R, Lee M-R, Peng S-M, Lee GH (1997) Organometallics 16:3469–3473

    CAS  Google Scholar 

  171. Rauchschwalbe G, Schlosser M (1975) Helv Chim Acta 58:1094–1099

    CAS  Google Scholar 

  172. Comins DL, Morgan LA (1991) Tetrahedron Lett 32:5919–5922

    CAS  Google Scholar 

  173. Beaulieu F, Snieckus V (1992) Synthesis 112–118

    Google Scholar 

  174. Turner JA (1983) J Org Chem 49:3401–3408

    Google Scholar 

  175. Mongin F, Trécourt F, Quéguiner G (1999) Tetrahedron Lett 40:5483–5486

    CAS  Google Scholar 

  176. Schlosser M, Rausis T (2004) Eur J Org Chem 1018–1024

    Google Scholar 

  177. Shutske GM, Roehr JE (1997) J Heterocycl Chem 34:789–795

    CAS  Google Scholar 

  178. Comins DL, Nolan JM (2001) Org Lett 3:4255–4257

    CAS  Google Scholar 

  179. Zhichkin P, Beer CMC, Rennels WM, Fairfax DJ (2006) Synlett 379–382

    Google Scholar 

  180. Wibaut JP, de Jonge AP, van der Voort HGP, Otto PPHL (1951) Recl Trav Chim Pays-Bas 70:1054–1066

    CAS  Google Scholar 

  181. den Hertog HJ, van der Plas HC (1965) Adv Heterocycl Chem 4:121–144

    Google Scholar 

  182. Reinecke MG (1982) Tetrahedron 38:427–498

    CAS  Google Scholar 

  183. Jamart-Gregoire B, Leger C, Caubère P (1990) Tetrahedron Lett 31:7599–7602

    CAS  Google Scholar 

  184. Streef JW, den Hertog HJ (1966) Recl Trav Chim Pays-Bas 85:803–816

    CAS  Google Scholar 

  185. Marsais F, Trécourt F, Bréant P, Quéguiner G (1988) J Heterocycl Chem 25:81–87

    CAS  Google Scholar 

  186. Caubère P (1993) Chem Rev 93:2317–2334

    Google Scholar 

  187. van der Plas HC (1978) Acc Chem Res 31:462–468

    Google Scholar 

  188. Streef JW, Den Hertog HJ, van der Plas HC (1985) J Heterocycl Chem 22:985–991

    CAS  Google Scholar 

  189. Utimoto K, Sakai N, Nozaki H (1974) J Am Chem Soc 96:5601–5602

    CAS  Google Scholar 

  190. Normant H (1957) Bull Soc Chim Fr 728–733

    Google Scholar 

  191. Overhoff J, Proost W (1938) Recl Trav Chim Pays-Bas 57:179–184

    CAS  Google Scholar 

  192. Wibaut JP, van der Voort HGP (1952) Recl Trav Chim Pays-Bas 71:798–804

    CAS  Google Scholar 

  193. Wibaut JP, Huls R (1952) Recl Trav Chim Pays-Bas 71:1021–1026

    CAS  Google Scholar 

  194. Wibaut JP, Heeringa LG (1955) Recl Trav Chim Pays-Bas 74:1003–1020

    CAS  Google Scholar 

  195. Kochetkov NK, Sokolov SD, Vagurtova NM, Nifantev EE (1960) Dokl Akad Nauk SSSR 133:598–601

    CAS  Google Scholar 

  196. Chambers RD, Hutchinson J, Musgrave WKR (1965) J Chem Soc 5040–5045

    Google Scholar 

  197. Dua SS, Gilman H (1968) J Organomet Chem 12:234–236

    CAS  Google Scholar 

  198. Berry DJ, Wakefield BJ (1969) J Chem Soc [C] 2342–2346

    Google Scholar 

  199. Furukawa N, Shibutani T, Fujihara H (1987) Tetrahedron Lett 28:5845–5848

    CAS  Google Scholar 

  200. Trécourt F, Breton G, Bonnet V, Mongin F, Marsais F, Quéguiner G (1999) Tetrahedron Lett 40:4339–4342

    Google Scholar 

  201. Catel D, Payen O, Chevallier F, Mongin F, Gros PC (2012) Tetrahedron 68:4018–4028

    CAS  Google Scholar 

  202. Murray A, Foreman WW, Langham W (1948) J Am Chem Soc 70:1037–1039

    CAS  Google Scholar 

  203. Gilman H, Spatz SM (1951) J Org Chem 16:1485–1494

    CAS  Google Scholar 

  204. Gilman H, Soddy TS (1957) J Org Chem 22:1715–1716

    CAS  Google Scholar 

  205. Wommack JB, Barbee TG, Thoeness DJ, Mcdonald MA, Pearson DE (1969) J Heterocycl Chem 6:243–245

    CAS  Google Scholar 

  206. Cottet F, Marull M, Lefebvre O, Schlosser M (2003) Eur J Org Chem 1559–1568

    Google Scholar 

  207. Tupitsyn IF, Zatspeina NN, Kirova AV, Kaminsky YL, Ivanenko AG (1973) Reakts Sposobn Org Soedin 10:143–162 [Chem Abstr 79:114928]

    Google Scholar 

  208. Schafman BS, Wenthold PG (2007) J Org Chem 72:1645–1651

    CAS  Google Scholar 

  209. Cottet F (2003) Doctoral Dissertation. Ecole Polytechnique Fédérale, Lausanne, pp 76–77

    Google Scholar 

  210. Cottet F (2002) Internal report, 3 March 2003

    Google Scholar 

  211. Cook JD, Wakefield BJ (1968) J Organomet Chem 13:15–23

    CAS  Google Scholar 

  212. Hertz HS, Kabacinski FF, Spoerri PE (1969) J Heterocycl Chem 6:239–241

    CAS  Google Scholar 

  213. Rho T, Abuh YF (1994) Synth Commun 24:253–256

    CAS  Google Scholar 

  214. Hirschberg A, Peterkoski A, Spoerri PE (1962) J Heterocycl Chem 2:209–210

    Google Scholar 

  215. Sandosham J, Undheim K (1994) Tetrahedron 50:275–284

    CAS  Google Scholar 

  216. Langley BW (1956) J Am Chem Soc 78:2136–2141

    CAS  Google Scholar 

  217. Ulbricht TLV (1959) Tetrahedron 6:225–231

    CAS  Google Scholar 

  218. Goudgaon NM, Naguib FNM, el Kouni MH, Schinazi RF (1993) J Med Chem 36:4250–4254

    CAS  Google Scholar 

  219. Asbun W, Binkley SB (1966) J Org Chem 31:2215–2219

    CAS  Google Scholar 

  220. Ondi L, Lefebvre O, Schlosser M (2004) Eur J Org Chem 3714–3718

    Google Scholar 

  221. Schlosser M, Lefebvre O, Ondi L (2006) Eur J Org Chem 1593–1598

    Google Scholar 

  222. Gros P, Fort Y, Caubère PJ (1997) Chem Soc Perkin Trans 1:3597–3600

    Google Scholar 

  223. Gros P, Viney C, Fort Y (2002) Synlett 628–630

    Google Scholar 

  224. Zoltewicz JA, Dill CD (1996) Tetrahedron 52:14469–14474

    CAS  Google Scholar 

  225. Mongin F, Rebstock A-S, Trécourt F, Quéguiner G, Marsais F (2004) J Org Chem 69:6766–6771

    CAS  Google Scholar 

  226. Sato N, Yue Q (2003) Tetrahedron 59:5831–5836

    CAS  Google Scholar 

  227. Couture A, Huguerre E, Grandclaudon P (1989) Tetrahedron Lett 30:183–184

    CAS  Google Scholar 

  228. Gilman H, Morton JW (1954) Org React 8:258–304

    Google Scholar 

  229. Godard A, Jacquelin J-M, Quéguiner G (1988) J Organomet Chem 354:273–285

    CAS  Google Scholar 

  230. Cailly T, Fabis F, Lemaître S, Bouillon A, Rault S (2005) Tetrahedron Lett 46:135–137

    CAS  Google Scholar 

  231. Penney JM (2004) Tetrahedron Lett 45:2667–2669

    CAS  Google Scholar 

  232. Comins DL, Killpack MO (1990) J Org Chem 55:69–73

    CAS  Google Scholar 

  233. Trécourt F, Mallet M, Marsais F, Quéguiner G (1988) J Org Chem 53:1367–1371

    Google Scholar 

  234. Gros P, Fort Y, Caubère P (1998) J Chem Soc Perkin Trans 1:1685–1690

    Google Scholar 

  235. Marsais F, Le Nard G, Quéguiner G (1982) Synthesis 235–237

    Google Scholar 

  236. Winkle MR, Ronald RC (1982) J Org Chem 47:2101–2108

    CAS  Google Scholar 

  237. Winkle MR, Ronald RC (1983) Tetrahedron 39:2031–2042

    Google Scholar 

  238. Trécourt F, Mallet M, Mongin O, Gervais B, Quéguiner G (1993) Tetrahedron 49:8373–8380

    Google Scholar 

  239. Iwao M, Kuraishi T (1983) Tetrahedron Lett 24:2649–2652

    CAS  Google Scholar 

  240. Miah MAJ, Snieckus V (1985) J Org Chem 50:5438–5440

    Google Scholar 

  241. Furukawa N, Shibutani T, Fujihara H (1989) Tetrahedron Lett 30:7091–7094

    CAS  Google Scholar 

  242. Schlosser M, Mongin F (2007) Chem Soc Rev 36:1161–1172

    CAS  Google Scholar 

  243. Estel L, Marsais F, Quéguiner G (1988) J Org Chem 53:2740–2744

    CAS  Google Scholar 

  244. Marsais F, Quéguiner G (1983) Tetrahedron 39:2009–2021 (spec. 2014–2015)

    CAS  Google Scholar 

  245. Barrière J-C, Bacqué E, Puchault G, Quenet Y, Molherat C, Cassayre J, Paris J-M (1998) Tetrahedron 54:12859–12886

    Google Scholar 

  246. Marzi E, Gorecka J, Schlosser M (2004) Synthesis 1609–1618

    Google Scholar 

  247. Bobbio C, Schlosser M (2005) J Org Chem 70:3039–3045

    CAS  Google Scholar 

  248. Marzi E, Schlosser M (2005) Tetrahedron 61:3393–3401

    CAS  Google Scholar 

  249. Marzi E, Mongin F, Spitaleri A, Schlosser M (2001) Eur J Org Chem 2911–2915

    Google Scholar 

  250. Schlosser M (2006) Angew Chem 118:5558–5572; Int Ed 45:5432–5446

    Google Scholar 

  251. Gorecka-Kobylinska J, Schlosser M (2009) J Org Chem 74:222–229

    CAS  Google Scholar 

  252. Schlosser M, Mongin F, Porwisiak J, Dmowski W, Büker HH, Nibbering NMM (1998) Chem Eur J 4:1281–1286

    CAS  Google Scholar 

  253. Ruzziconi R, Spizzichino S, Lunazzi L, Mazzanti A, Schlosser M (2009) Chem Eur J 15:2645–2652

    CAS  Google Scholar 

  254. Mazzanti A, Lunazzi L, Ruzziconi R, Spizzichino S, Schlosser M (2010) Chem Eur J 16:9186–9192

    CAS  Google Scholar 

  255. Ruzziconi R, Spizzichino S, Mazzanti A, Lunazzi L, Schlosser M (2010) Org Bioorg Chem 8:4463–4471

    CAS  Google Scholar 

  256. Cottet F, Schlosser M. (2004), unpublished results

    Google Scholar 

  257. Porwisiak J, Dmowski W (1994) Tetrahedron 50:12259–12266

    CAS  Google Scholar 

  258. Cottet F, Marull M, Mongin F, Espinosa D, Schlosser M (2004) Synthesis 1619–1624

    Google Scholar 

  259. Cottet F, Schlosser M (2004) Tetrahedron 60:11869–11874

    CAS  Google Scholar 

  260. Cottet F, Schlosser M (2004) Eur J Org Chem 3793–3798

    Google Scholar 

  261. Castagnetti E, Schlosser M (2001) Eur J Org Chem 691–695

    Google Scholar 

  262. Schlosser M, Castagnetti E (2001) Eur J Org Chem 3991–3997

    Google Scholar 

  263. Castagnetti E, Schlosser M (2002) Chem Eur J 8:799–804

    CAS  Google Scholar 

  264. Leroux F, Castagnetti E, Schlosser M (2003) J Org Chem 68:4693–4699

    CAS  Google Scholar 

  265. Shimizu M, Hiyama T (2006) Angew Chem 118:5558–5572; Int Ed 45:5432–5446

    Google Scholar 

  266. Manteau B, Genix P, Brelot L, Voss J-P, Pazenok S, Giornal F, Leuenberger C, Leroux FR (2010) Eur J Org Chem 6043–6066

    Google Scholar 

  267. Büker HH, Nibbering NMM, Espinosa D, Mongin F, Schlosser M (1997) Tetrahedron Lett 39:8519–8522

    Google Scholar 

  268. Schlosser M, Marzi E, Cottet F, Büker HH, Nibbering NMM (2001) Chem Eur J 7:3511–3516

    CAS  Google Scholar 

  269. Mallet M (1991) J Organomet Chem 406:49–56

    CAS  Google Scholar 

  270. Gros P, Fort Y, Quéguiner G, Caubère P (1995) Tetrahedron Lett 36:4791–4794

    CAS  Google Scholar 

  271. Marsais F, Bréant P, Ginguène A, Quéguiner G (1981) J Organomet Chem 216:139–147

    CAS  Google Scholar 

  272. Choppin S, Gros P, Fort Y (2001) Eur J Org Chem 603–606

    Google Scholar 

  273. Radinov R, Chanev C, Haimova M (1991) J Org Chem 56:4793–4796

    CAS  Google Scholar 

  274. Cale AD, Gero TW, Walker KR, Lo YS, Welstead WJ, Jaques LW, Johnson AF, Leonard CA, Nolan JC, Johnson DN (1989) J Med Chem 32:2178–2199 (spec. 2198)

    CAS  Google Scholar 

  275. Murata N, Sugihara T, Kondo Y, Sakamoto T (1997) Synlett 298–300

    Google Scholar 

  276. Güngör T, Marsais F, Quéguiner G (1981) J Organomet Chem 215:139–150

    Google Scholar 

  277. Marzi E, Bigi A, Schlosser M (2001) Eur J Org Chem 1371–1376

    Google Scholar 

  278. Marzi E (2001) Doctoral Dissertation. Université de Lausanne, pp 43–46, 91–96

    Google Scholar 

  279. Marsais F, Laperdix B, Güngör T, Mallet M, Quéguiner G (1982) J Chem Res (S) 278–279

    Google Scholar 

  280. Menzel K, Fisher EL, DiMichele L, Frantz DE, Nelson TD, Kress MH (2006) J Org Chem 71:2188–2199

    CAS  Google Scholar 

  281. Mallet M, Quéguiner G (1982) Tetrahedron 39:3035–3042

    Google Scholar 

  282. Effenberger F, Daub W (1991) Chem Ber 124:2119–2125

    CAS  Google Scholar 

  283. Schlosser M, Marull M (2003) Eur J Org Chem 1569–1575

    Google Scholar 

  284. Marzi E, Bobbio C, Cottet F, Schlosser M (2005) Eur J Org Chem 2116–2123

    Google Scholar 

  285. Marzi E (2001) Doctoral Dissertation. Université de Lausanne, pp 50–51, 101–102

    Google Scholar 

  286. Wotiz JH, Huba F (1959) J Org Chem 24:595–598

    CAS  Google Scholar 

  287. Moses P, Gronowitz S (1961) Arkiv Kemi 19:119–132

    Google Scholar 

  288. Fröhlich J, Hametner C, Kalt W (1996) Monatsh Chem 325–330

    Google Scholar 

  289. Rocca P, Cochennec C, Marsais F, Thomas-dit-Dumont L, Mallet M, Godard A, Quéguiner G (1993) J Org Chem 59:7832–7838

    Google Scholar 

  290. Arzel E, Rocca P, Marsais F, Godard A, Quéguiner G (1999) Tetrahedron 55:12149–12156

    CAS  Google Scholar 

  291. Mallet M, Branger G, Marsais F, Quéguiner G (1990) J Organomet Chem 382:319–332

    CAS  Google Scholar 

  292. Mongin F, Desponds O, Schlosser M (1996) Tetrahedron Lett 37:2767–2770

    CAS  Google Scholar 

  293. Heiss C, Rausis T, Schlosser M (2005) Synthesis 617–621

    Google Scholar 

  294. Awad H, Mongin F, Trécourt F, Quéguiner G, Marsais F (2004) Tetrahedron Lett 45:7873–7877

    CAS  Google Scholar 

  295. Marull M, Schlosser M (2004) Eur J Org Chem 1008–1013

    Google Scholar 

  296. Wada A, Yamamoto J, Hamaoka Y, Ohki K, Nagai S, Kanatomo S (1990) J Heterocycl Chem 27:1831–1835

    CAS  Google Scholar 

  297. Plé N, Turck A, Couture K, Quéquiner G (1996) Synthesis 838–842

    Google Scholar 

  298. Lee JI, Cho SH (1996) Bull Korean Chem Soc 17:868–869

    CAS  Google Scholar 

  299. Plé N, Turck A, Bardin F, Quéquiner G (1992) J Heterocycl Chem 29:467–470

    Google Scholar 

  300. Schlosser M, Wei H-x (1997) Tetrahedron 53:1735–1742

    CAS  Google Scholar 

  301. Plé N, Turck A, Heynderickx A, Quéquiner G (1997) J Heterocycl Chem 34:551–556

    Google Scholar 

  302. Plé N, Turck A, Martin P, Barbey S, Quéquiner G (1993) Tetrahedron Lett 34:1605–1608

    Google Scholar 

  303. Abramovitch RA, Knaus EE (1975) J Heterocycl Chem 12:683–690

    CAS  Google Scholar 

  304. Kessar SV, Singh P, Singh KN, Dutt M (1991) J Chem Soc Chem Commun 570–571

    Google Scholar 

  305. Kessar SV, Singh P (1997) Chem Rev 97:721–737

    CAS  Google Scholar 

  306. Vedejs E, Chen X (1996) J Am Chem Soc 118:1809–1810

    CAS  Google Scholar 

  307. Taylor SL, Lee DY, Martin JC (1983) J Org Chem 48:4156–4158

    CAS  Google Scholar 

  308. Schlosser M, Schneider P (1979) Angew Chem 91:515–517; Int Ed (1966) 18:489–490

    Google Scholar 

  309. Stout DM, Takaya T, Meyers AI (1975) J Org Chem 40:563–569

    CAS  Google Scholar 

  310. Schmidt RR, Berger G (1976) Chem Ber 109:2936–2947

    CAS  Google Scholar 

  311. Comins DL, Weglarz MA, O’Connor S (1988) Tetrahedron Lett 29:1751–1754

    CAS  Google Scholar 

  312. Meghani P, Joule JA (1988) J Chem Soc Perkin Trans 1:1–8

    Google Scholar 

  313. Moret E, Schneider P, Margot C, Stähle M, Schlosser M (1985) Chimia 39:231–232

    CAS  Google Scholar 

  314. Meyers AI, Edwards PD, Bailey TR, Jagdmann GE (1985) J Org Chem 50:1019–1026

    CAS  Google Scholar 

  315. Zhao D, You J, Hu C (2011) Chem Eur J 17:5466–5492

    CAS  Google Scholar 

  316. Kowada T, Matsuyama Y, Ohe K (2008) Synlett 1902–1906

    Google Scholar 

  317. Kondolff I, Doucet H, Santelli M (2008) J Heterocycl Chem 45:109–118

    CAS  Google Scholar 

  318. Billingsley K, Buchwald SL (2007) J Am Chem Soc 129:3358–3366

    CAS  Google Scholar 

  319. Jäger M, Ericksson L, Bergquist J, Johansson O (2007) J Org Chem 72:10227–10230

    Google Scholar 

  320. Daykin LM, Siddle JS, Ankers AL, Batsanov AS, Bryce MR (2010) Tetrahedron 66:668–675

    CAS  Google Scholar 

  321. Mai W, Yuan J, Li Z, Sun G, Qu L (2012) Synlett 145–149

    Google Scholar 

  322. Ackermann L, Potukuchi HK, Kapdi AR, Schulzke C (2010) Chem Eur J 16:3300–3303

    CAS  Google Scholar 

  323. Çalimsiz S, Sayah M, Mallik D, Organ MG (2010) Angew Chem 122:2058–2061; Int Ed 49:2014–2017

    Google Scholar 

  324. Rieth RD, Mankad NP, Calimano E, Sadighi JP (2004) Org Lett 6:3981–3983

    CAS  Google Scholar 

  325. Choppin S, Gros P, Fort Y (2000) Org Lett 2:803–805

    CAS  Google Scholar 

  326. Kuo G-H, Wang A, Emanuel S, DeAngelis A, Zhang R, Connolly PJ, Gruninger RH, Sechler J, Fuentes-Pesquera A, Johnson D, Middleton SA, Jolliffe L, Chen X (2005) J Med Chem 48:1886–1900

    CAS  Google Scholar 

  327. Pierrat P, Gros PC, Fort Y (2005) Org Lett 7:697–700

    CAS  Google Scholar 

  328. Loüerat F, Gros PC (2010) Tetrahedron Lett 51:3558–3560

    Google Scholar 

  329. Jiang W, Guan J, Macielag MJ, Zhang S, Qiu Y, Kraft P, Battacharjee S, John TM, Haynes-Johnson D, Lundeen S, Sui Z (2005) J Med Chem 48

    Google Scholar 

  330. Akita Y, Inoue A, Yamamoto K, Ohta A, Kurihara T, Shimizu M (1985) Heterocycles 23:2327–2333

    CAS  Google Scholar 

  331. Li W, Nelson DP, Jensen MS, Hoerrner RS, Javadi GJ, Cai D, Larsen RD (2003) Org Lett 5:4835–4837

    CAS  Google Scholar 

  332. Čerňa I, Pohl R, Klepetářová B, Hocek M (2006) Org Lett 8:5389–5392

    Google Scholar 

  333. Sahnoun S, Messaoudi S, Brion J-D, Alami M (2009) Org Biomol Chem 7:4271–4278

    CAS  Google Scholar 

  334. Derridj F, Roger J, Geneste F, Djebbar S, Doucet H (2009) J Organomet Chem 694:455–465

    CAS  Google Scholar 

  335. Fournier dit Chabert J, Joucla L, David E, Lemaire M (2004) Tetrahedron 60:3221–3230

    Google Scholar 

  336. Strotman NA, Chobanian HR, Guo Y, He J, Wilson JE (2010) Org Lett 12:3578–3581

    CAS  Google Scholar 

  337. Huang J, Chan J, Chen YX, Borths CJ, Baucom KD, Larsen RD, Faul MM (2010) J Am Chem Soc 132:3674–3675

    CAS  Google Scholar 

  338. Do H-Q, Khan RMK, Daugulis O (2008) J Am Chem Soc 130:15185–15192

    CAS  Google Scholar 

  339. Campeau L-C, Rousseaux S, Fagnou K (2005) J Am Chem Soc 127:18020–18021

    CAS  Google Scholar 

  340. Leclerc J-P, Fagnou K (2006) Angew Chem 118:7945–7950; Int Ed 45:7781–7786

    Google Scholar 

  341. Larivée A, Mousseau JJ, Charette AB (2008) J Am Chem Soc 130:52–54

    Google Scholar 

  342. Xu J, Cheng G, Su D, Liu Y, Wang X, Hu Y (2009) Chem Eur J 15:13105–13110

    CAS  Google Scholar 

  343. Yanagisawa S, Ueda K, Taniguchi T, Itami K (2008) Org Lett 10:4673–4676

    CAS  Google Scholar 

  344. Tobisu M, Hyodo N, Chatani N (2009) J Am Chem Soc 131:12070–12071

    CAS  Google Scholar 

  345. Berman AM, Lewis JC, Bergman RG, Ellman JA (2008) J Am Chem Soc 130:14926–14927

    CAS  Google Scholar 

  346. Li M-Y, Hua R (2009) Tetrahedron Lett 50:1478–1481

    CAS  Google Scholar 

  347. Miura H, Wada K, Hosokawa S, Inoue M (2010) Chem Eur J 16:4186–4189

    CAS  Google Scholar 

  348. Kasahara A (1968) Bull Chem Soc Jpn 41:1272

    CAS  Google Scholar 

  349. Hartwell GE, Lawrence RV, Smas MJ (1970) Chem Commun 912–912

    Google Scholar 

  350. Li W, Yin Z, Jiang X, Sun P (2011) J Org Chem 76:8543–8548

    CAS  Google Scholar 

  351. Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300–2301

    CAS  Google Scholar 

  352. Nakao Y (2011) Synthesis 1951–1955

    Google Scholar 

  353. Jordan RF, Taylor DF (1989) J Am Chem Soc 111:778–779

    CAS  Google Scholar 

  354. Rodewald S, Jordan RF (1994) J Am Chem Soc 116:4491–4492

    CAS  Google Scholar 

  355. Guan B-T, Hou Z (2011) J Am Chem Soc 133:18086–18089

    CAS  Google Scholar 

  356. Lewis JC, Bergman RG, Ellman JA (2007) J Am Chem Soc 129:5332–5333

    CAS  Google Scholar 

  357. Dudkina YB, Mikhaylov DY, Gryaznova TV, Sinyashin OG, Vicic DA, Budnikova YH (2012) Eur J Org Chem 2114–2117

    Google Scholar 

  358. Nakao Y, Yamada Y, Kashihara N, Hiyama T (2010) J Am Chem Soc 132:13666–13668

    CAS  Google Scholar 

  359. Grigg R, Savic V (1997) Tetrahedron Lett 38:5737–5740

    CAS  Google Scholar 

  360. Ye M, Gao G-L, Yu J-Q (2011) J Am Chem Soc 133:6964–6967

    CAS  Google Scholar 

  361. Moore EJ, Pretzer WR, O’Connell TJ, Harris J, LaBounty L, Chou L, Grimmer SS (1992) J Am Chem Soc 114:5888–5890

    CAS  Google Scholar 

  362. Stuart DR, Villemure E, Fagnou K (2007) J Am Chem Soc 129:12072–12073

    CAS  Google Scholar 

  363. Potavathri S, Pereira KC, Govelsky SI, Pike A, LeBris AP, DeBoef B (2010) J Am Chem Soc 132:14676–14681

    CAS  Google Scholar 

  364. Han W, Ofial AR (2011) Synlett

    Google Scholar 

  365. Xi P, Yang F, Qin S, Zhao D, Lan J, Gao G, Hu C (2010) J Am Chem Soc 132:1822–1824

    CAS  Google Scholar 

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  1. Swiss Federal Institute of Technology, 1015, Lausanne, Switzerland

    Manfred Schlosser

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  1. Vienna University of Technology Institute of Applied Synthetic Chemistry, Vienna, Austria

    Michael Schnürch

  2. Vienna University of Technology Institute of Applied Synthetic Chemistry, Vienna, Austria

    Marko D. Mihovilovic

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Schlosser, M. (2013). Reactions of Pyridines, Benzopyridines, and Azapyridines with Organomagnesiums and Organolithiums. In: Schnürch, M., Mihovilovic, M. (eds) Metalation of Azines and Diazines. Topics in Heterocyclic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2012_96

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