Tin in Organic Synthesis: Cross-Coupling of Organotin Compounds for Carbon Carbon Bond Formation

Tin Chemistry: Fundamentals, Frontiers, and Applications

Volumn , Issue , 2008, Pages 561-578

  Espinet, Pablo ^a   Genov, Miroslav ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Alkenyl aryl and alkenyl heteroaryl bonds; Aryl iodide starter species; Chiral (acyloxy)borane (CAB) catalysts; Dibutylstannylene acetal formation; Lewis acid mediated additions of allenylstannanes; Oxocarbenium systems crotylation reactions; Palladium catalyzed cascade cyclization anion capture processes; Tin in organic synthesis; Vinyl halide starter species

Indexed keywords

EID: 84891321885     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470758090.ch5     Document Type: Chapter

References (117)

1. E.-I. Negishi, J. Organomet. Chem. 2002, 653, 34.
2. N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, and A. Suzuki, J. Am. Chem. Soc. 1989, 111, 314.
3. Y. Hatanaka and T. Hiyama, Pure Appl. Chem. 1994, 66, 1471;
4. Y. Hanataka and T. Hiyama, Synlett 1991, 845;
5. T. Hiyama in Metal-Catalyzed Cross-Coupling Reactions, F. Diederich and P. J. Stang (Eds), Wiley-VCH, Weinheim, 1998, Chapter 10;
6. T. Hiyama and E. Shirakawa, Topp. Curr. Chem. 2002, 219, 61.
7. K. Sonogashira, J. Organomet. Chem. 2002, 653, 46;
8. R. R. Tykwinski, Angew. Chem. Int. Ed. 2003, 42, 1566.
9. K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374;
10. M. Yamamura, I. Moritani, and S.-I. Murahashi, J. Organomet. Chem. 1975, 91, C39;
11. J. F. Fauvarque and A. Jutand, Bull. Soc. Chim. Fr. 1976, 765;
12. A. Sekiya and N. Ishikawa, J. Organomet. Chem. 1976, 118, 349.
13. E. Negishi, Acc. Chem. Res. 1982, 15, 340;
14. E. Negishi, M. Qian, F. Zeng, L. Anastasia, and D. Babinski, Org. Lett. 2003, 5, 1597, and references therein;
15. E. Negishi and L. Anastasia, Chem. Rev. 2003, 103, 1979.
16. Leading references on palladium-catalyzed couplings of organoindium compounds: (a) I. Pérez, J. P. Sestelo, and L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155;
17. K. Takami, H. Yorimitsu, H. Shinokubo, S. Matsubara, and K. Oshima, Org. Lett. 2001, 3, 1997;
18. U. Lehmann, S. Awasthi, and T. Minehan, Org. Lett. 2003, 5, 2405;
19. P. Ho Lee, S. W. Lee, and D. Seomoon, Org. Lett. 2003, 5, 4963.
20. Iron-catalyzed cross-couplings of alkyl-Grignards: A. Fürstner and A. Leitner, Angew. Chem. 2002, 114, 632;
21. Angew. Chem. Int. Ed. 2002, 41, 609;
22. A. Fürstner, A. Leitner, M. Méndez, and H. Krause, J. Am. Chem. Soc. 2002, 124, 13856.
23. J. K. Stille, Angew. Chem. 1986, 98, 504;
24. Angew. Chem. Int. Ed. Engl 1986, 25, 508.
25. V. Farina in Comprehensive Organometallic Chemistry II, Vol. 12, E.W. Abel, F. G. A. Stone, and G.Wilkinson (Eds), Pergamon, Oxford, 1995, Chapter 3.4.
26. T. N. Mitchell, Synthesis 1992, 803;
27. T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions , F. Diederich and P. J. Stang (Eds), Wiley-VCH, New York, 1998, Chapter 4.
28. V. Farina, V. Krishnamurthy, and V. J. Scott, The Stille Reaction, Wiley, New York, 1998.
29. D. Azarian, S. S. Dua, C. Eaborn, and D. R. M. Walton, J. Organomet. Chem. 1976, 117, C55.
30. M. Kosugi, K. Sasazawa, Y. Shimizu, and T. Migita, Chem. Lett. 1977, 301;
31. M. Kosugi, Y. Shimizu, and T. Migita, Chem. Lett. 1977, 1423.
32. M. Kosugi and K. Fugami, J. Organomet. Chem. 2002, 653, 50.
33. D. Milstein and J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636.
34. V. Farina, V. Krishnamurthy, and W. K. Scott, Organic Reactions, Vol. 50, John Wiley & Sons, Inc., New York, 1997.
35. J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Ltd, Chichester, 1995.
36. K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996;
37. K. C. Nicolaou and S. A. Snyder, Classics in Total Synthesis II, Wiley-VCH, Weinheim, 2003.
38. M. A. J. Duncton, and G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1999, 1235.
39. M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, and S. J. Danishefsky, J. Am. Chem. Soc. 1996, 118, 9509.
40. K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, and P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419;
41. K. C. Nicolaou, A. D. Piscopio, P. Bertinato, T. K. Chakraborty, N. Minowa, and K. Koide, Chem. Eur. J. 1995, 1, 318.
42. J. W. Labadie and J. K. Stille, J. Am. Chem. Soc. 1983, 105, 6129.
43. J. Ye, R. K. Bhatt, and J. R. Falck, J. Am. Chem. Soc. 1994, 116, 1;
44. J. Ye, R. K. Bhatt, and J. R. Falck, Tetrahedron Lett. 1993, 34, 8007.
45. J. W. Labadie and J. K. Stille, J. Am. Chem. Soc. 1983, 105, 6129;
46. K. Kells and J. M. Chong, J. Am. Chem. Soc. 2004, 126, 15666.
47. P. Espinet and A. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704, and references cited herein.
48. R. Alvarez, O. N. Faza, C. S. Lopez, and A. R. de Lera, Org. Lett. 2006, 35.
49. A. Nova, G. Ujaque, F. Maseras, A. Lledós, and P. Espinet, J. Am. Chem Soc 2006, 128, 14571.
50. A minireview on the use of anhydrides, esters, and carbonic acid derivatives as substrates for the oxidative addition to Pd0: A. Zapf, Angew. Chem. 2003, 115, 5552;
51. Angew. Chem. Int. Ed. 2003, 42, 5394;
52. Stille coupling of sulfonyl chlorides: S. R. Dubbaka and P. Vogel, J. Am. Chem. Soc. 2003, 125, 15292.
53. H. Kurosawa, S. Ogoshi, Y. Kawasaki, S. Murai, M. Miyoshi, and I. Ikeda, J. Am. Chem. Soc. 1990, 112, 2813;
54. H. Kurosawa, H. Kajimura, S. Ogoshi, H. Yoneda, K. Miki, N. Kasai, S. Murai, and I. Ikeda, J. Am. Chem. Soc. 1992, 114, 8417.
55. A. Vitagliano, B. Åkermark, and S. Hansson, Organometallics, 1991, 10, 2592.
56. A. L. Casado, P. Espinet, and A. M. Gallego, J. Am. Chem. Soc. 2000, 122, 11771.
57. A. L. Casado and P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978.
58. For a review about the mechanisms of the cleavage of carbon-tin bonds, see M. Gielen, J. Braz. Chem. Soc. 2003, 14, 870.
59. D. Coulson, Inorg. Synth. 1972, 13, 121.
60. This is a dinuclear complex of formula [Pd2(dba)3•dba]: Y. Takahashi, T. Ito, S. Sakai, and Y. Ishii, J. Chem. Soc., Chem. Commun 1970, 1065. After recrystallization, [Pd2(dba)3•(solv)] (solv = CH2Cl2, CHCl3, benzene, toluene) are obtained:
61. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnet, and J. A. Ibers, J. Organomet. Chem. 1974, 65, 253;
62. M. C. Mazza and C. G. Pierpont, J. Chem. Soc., Chem. Commun. 1973, 207;
63. M. C. Mazza and C. G. Pierpont, Inorg. Chem. 1974, 13, 1891.
64. See also: A. M. Echavarren and J. K. Stille, J. Organomet. Chem. 1988, 356, C35.
65. Tris(dibenzylideneacetone)palladium(0), [Pd(dba)3], has been prepared by heating [Pd(dba)2] with excess dba in benzene: M. C. Mazza and C. G. Pierpont, Inorg. Chem. 1973, 12, 2955.
66. M. Kharash, R. Seyler, and F. Mayo, J. Am. Chem. Soc. 1938, 60, 882.
67. A. Schoeberg, I. Bartoletti, and R. Heck, J. Org. Chem. 1974, 39, 3318.
68. K. Lau, P. Wong, and J. K. Stille, J. Am. Chem. Soc., 1976, 98, 5832;
69. P. Fitton, J. McKeon, and B. Ream, J. Chem. Soc., Chem. Commun. 1969, 370.
70. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, and K. Hirotsu, J. Am. Chem. Soc, 1984, 106, 158.
71. W. Dent, R. Long, and A. Wilkinson. J. Chem. Soc. 1964, 1585.
72. Review of cross-coupling reactions of aryl chlorides: A. F. Littke and G. C. Fu, Angew. Chem. 2002, 114, 4350-4386;
73. Angew. Chem. Int. Ed. 2002, 41, 4177.
74. The Stille coupling of activated aryl fluorides has been recently found to be possible simply by using [Pd(PPh3)4] as the catalyst: Y. M. Kim and S. Yu, J. Am. Chem. Soc. 2003, 125, 1696.
75. D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203;
76. Angew. Chem. Int. Ed. 1999, 38, 3018;
77. D. J. Cárdenas, Angew. Chem. 2003, 115, 398;
78. Angew. Chem. Int. Ed. 2003, 42, 384.
79. A. Littke and G. Fu, Angew Chem., Int. Ed. 1999, 38, 2411;
80. A. Littke, L. Schwarz, and G. Fu, J. Am. Chem. Soc. 2002, 124, 6343.
81. H. Tang, K. Menzel, and G. C. Fu, Angew. Chem. Int. Ed. 2003, 42, 5079.
82. R. Bedford, C. Cazin, and S. Hazelwood (née Welch), Chem. Commun. 2002, 2508.
83. W. Su, S. Urgaonkar, and J. Verkade, Org. Lett. 2004, 6, 1421;
84. W. Su, S. Urgaonkar, P. McLaughlin, and J. Verkade, J. Am. Chem. Soc. 2004, 126, 16433.
85. A. Hillier, G. Grasa, M. Viciu, H. Lee, Ch. Yang, and S. Nolan, J. Organomet. Chem. 2002, 653, 69, and references cited herein.
86. G. Grasa and S. Nolan, Org. Lett. 2001, 3, 119.
87. V. Farina and B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585.
88. V. Farina and G. Roth, Tetrahedron Lett. 1991, 32, 4243.
89. P. Arsenyan, M. Ikaunieks, and S. Belyakov, Tetrahedron Lett. 2007, 48, 961.
90. E. Quéron and R. Lett, Tetrahedron Lett. 2004, 45, 4539.
91. J.-M. Chrétien, A. Mallinger, F. Zammattio, E. Le Grognec, M. Paris, G. Montavonc, and J.-P. Quintarda, Tetrahedron Lett. 2007, 48, 1781.
92. M. M. Dell'Anna , A. Lofù, P. Mastrorilli, V. Mucciante, and C. F. Nobile, J. Organomet. Chem 2006, 691, 131.
93. K. Lau and P. Chiu, Tetrahedron Lett. 2007, 48, 1813.
94. H. Azinian, C. Eaborn, and A. Pidcock, J. Organomet. Chem. 1981, 215, 49;
95. R. Sustman, J. Lau, and M. Zipp, Tetrahedron Lett. 1986, 27, 5207;
96. R. van Asselt and C. Elsevier, Tetrahedron 1994, 50, 323.
97. J.-H. Li, Y. Liang, D.-P. Wang, W.-J. Liu,Y.-X. Xie, and D.-L. Yin, J. Org. Chem. 2005, 70, 2832.
98. G. Roth and V. Farina, Tetrahedron Lett. 1995, 36, 2191.
99. A. Herve, A. Rodriguez, and E. Fouquet, . Org. Chem. 2005, 70, 1953.
100. V. Farina and G. P. Roth, Adv. Metalorg. Chem. 1996, 5, 1;
101. V. Farina, Pure Appl. Chem. 1996, 68, 73.
102. V. Farina, S. Kapadia, B. Krishnan, C. Wang, and L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905.
103. A. L. Casado and P. Espinet, Organometallics, 2003, 22, 1305-1309.
104. S. Mee, V. Lee, and J. Baldwin, Angew. Chem. Int. Ed. 2004, 43, 1132.
105. W-S. Kim, H-J. Kim, and C-G. Cho, J. Am. Chem. Soc. 2003, 125, 14288.
106. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250-6284, and references cited herein.
107. M. Larhed, C. Moberg, and A. Hallberg, Acc. Chem. Res. 2002, 35, 717, and references cited herein.
108. M. Larhed and A. Hallberg, J. Org. Chem 1996, 61, 9582.
109. M. Larhed, G. Lindenberg, and A. Hallberg, Tetrahedron Lett. 1996, 37, 8219.
110. M. Larhed, M. Hoshino, S. Hadida, D. Curran, and A. Hallberg, J. Org. Chem. 1997, 62, 5583.
111. K. Olofsson, S. Kim, M. Larhed, D. Curran, and A. Hallberg, J. Org. Chem 1999, 64, 4539.
112. K. Nicolaou, P. Bulger, and D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4442, and references cited herein.
113. E. Piers, R. Friesen, and B. Keay, J. Chem. Soc. Chem. Commun. 1985, 809.
114. For a recent review for the application of the Stille reaction in the synthesis of complex natural products see: M. Vinícius and N. de Souza, Curr. Org. Synth. 2006, 3, 313.
115. H. Fuwa, N. Kainuma, K. Tachibana, and M. Sasaki, J. Am. Chem.Soc. 2002, 124, 14983, and references therein.
116. I. Kadota, H. Takamura, K. Sato, A. Ohno, K. Matsuda, and Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 46;
117. I. Kadota, H. Takamura, K. Sato, A. Ohno, K. Matsuda, M. Satake, and Y. Yamamoto, J. Am. Chem. Soc.2003, 125, 11893.