Tin in Organic Synthesis: New Trends in the Synthesis of Solid-Supported Organotin Reagents and Interest of their Use in Organic Synthesis in a Concept of Green Chemistry

Tin Chemistry: Fundamentals, Frontiers, and Applications

Volumn , Issue , 2008, Pages 607-621

  Chrétien, Jean Mathieu ^a   Kilburn, Jeremy D ^b   Zammattio, Françoise ^a   Le Grognec, Erwan ^a   Quintard, Jean Paul ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

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: 70449339013     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470758090.ch5     Document Type: Chapter

References (147)

1. M. Pereyre, J.-P. Quintard, and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987;
2. A. G. Davies, Organotin Chemistry, VCH, Weinheim, 1997.
3. W. P. Neumann, Synthesis, 665, (1987);
4. D. P. Curran Synthesis, 417, (1988).
5. D. P. Curran, Synthesis, 489, (1988).
6. V. Darmency and P. Renaud, Topics in Current Chemistry, 263, 71, (2006).
7. J. K. Stille, Angew. Chem. Int. Ed., 25, 508, (1986);
8. V. Farina, V. Krishnamurthy, and W. J. Scott, 'The Stille Reaction', Organic Reactions, 50, 1, (1997).
9. J. B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075, (1985);
10. J.-L. Parrain, I. Beaudet, A. Ducĥene, S. Watrelot, and J.-P. Quintard, Tetrahedron Lett., 34, 5445 (1993).
11. K. C. Nicolaou, P. G. Bulger, and D. Sarlah, Angew. Chem. Int. Ed., 44, 4442, (2005).
12. Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207, (1993);
13. J. A. Marshall, Chem. Rev., 96, 31, (1996);
14. E. J. Thomas, Chem. Commun., 411, (1997);
15. S. E. Denmark and J. Fu, Chem. Rev., 103, 2763, (2003);
16. M. Booth, C. Brain, P. Castreno, S. Donnelly, E. K. Dorling, O. Germay, L. Hobson, N. Kumar, N. Martin, C. Moore, D. Negi, E. J. Thomas, and A. Weston, Pure Appl. Chem., 78, 2015, (2006);
17. E. J. Thomas, Chem. Record, 7, 115, (2007);
18. V. Fargeas, F. Zammattio, J.-M. Chrétien, M.-J. Bertrand, M. Paris, and J.-P. Quintard, Eur. J. Org. Chem., 1681, (2008).
19. S. David and S. Hanessian, Tetrahedron, 41, 643, (1985).
20. K. V. V. Prasada Rao, R. Dandala, V. K. Handa, I. V. Subramanyeswara Rao, A. Rani, S. Shivashankar, and A. Naidu, Synlett, 1289, (2007).
21. Étain et Organostanniques : Mise au point préliminaire-Critères d'Hygiène de l'Environnement, Organisation Mondiale de la Santé, Genève, vol 15, 1981.
22. C. Alzieu, Y. Thibaud, M. Heral, and B. Boutier, Rev. Trav. Inst. P̂eches Marit., 44, 301, (1980);
23. R. B. Laughlin Jr., and O. Linden, Ambio, 14, 88, (1985).
24. R.J. Maguire, Environ. Sci. Technol., 18, 291, (1984);
25. R. J. Amouroux, E. Tessier, and O. F. X. Donard, Environ. Sci. Technol., 34, 988, (2000).
26. J. Lipowitz and S. A. Bowman, J. Org. Chem., 38, 162, (1973);
27. E. J. Corey and J. W. Suggs, J. Org. Chem., 40, 2554, (1975);
28. G. Stork and P. M. Sher, J. Am. Chem. Soc., 108, 303, (1986);
29. D. S. Hays and G. C. Fu, Tetrahedron, 55, 8815, (1999);
30. W. P. Gallagher, I. Terstiege, and R. E. Maleczka, Jr., J. Am. Chem. Soc., 123, 3194, (2001);
31. W. P. Gallagher and R. E. Maleczka, Jr., J. Org. Chem., 70, 841, (2005).
32. D. Milstein and J. K. Stille, J. Am. Chem. Soc., 100, 3636, (1978);
33. J. E. Leibner and J. Jacobus, J. Org. Chem., 44, 449, (1979).
34. B. S. Edelson, B. M. Stoltz, and E. J. Corey, Tetrahedron Lett., 40, 6729, (1999);
35. A. F. Littke and G. C. Fu, Angew. Chem. Int. Ed., 38, 2411, (1999).
36. D. C. Harrowven and I. L. Guy, Chem. Commun., 1968, (2004);
37. D. C. Harrowven and I. L. Guy, Brit. Patent, GB2412074, 2005.
38. J. M. Berge and S. M. Roberts, Synthesis, 471, (1979).
39. V. Coeffard, E. Le Grognec, I. Beaudet, M. Lepeltier, V. Leat-Crest, and J.-P. Quintard, Synthesis, 24, 4151, (2006).
40. F. Ferkous, D. Messadi, B. De Jeso, M. Degueil-Castaing, and B. Maillard, J. Organometal. Chem., 420, 315, (1991);
41. F. Ferkous, M. Degueil-Castaing, H. Deleuze, and B. Maillard, Main Group Met. Chem., 20, 75, (1997);
42. J. Light, and R. Breslow, Tetrahedron Lett., 31, 2957, (1990).
43. R. Rai and D. B. Collum, Tetrahedron Lett., 35, 6221, (1994);
44. D. L. J. Clive and J. Wang, J. Org. Chem., 67, 1192, (2002).
45. E. Vedejs, S. M. Duncan, and A. R. Haight, J. Org. Chem., 58, 3046, (1993).
46. S. Suga, T. Manabe, and J.-I. Yoshida, Chem. Commun., 1237, (1999).
47. X. Han, G. A. Hartmann, A. Brazzale, and R. D. Gaston, Tetrahedron Lett., 42, 5837, (2001).
48. E. Vedejs, A. R. Haight, and W. O. Moss, J. Am. Chem. Soc., 114, 6556, (1992);
49. M. S. Jensen, C. Yang, Y. Hsiao, N. Rivera, K. M.Wells, J. Y. L. Chung, N. Yasuda, D. L. Hughes, and P. J. Reider, Org. Lett., 2, 1081, (2000).
50. S. Gastaldi and D. Stien, Tetrahedron Lett., 43, 4309, (2002);
51. D. Stien and S. Gastaldi, J. Org. Chem., 69, 4464, (2004).
52. D. P. Curran, S. Hadida, S.-Y. Kim, and Z. Luo, J. Am. Chem. Soc., 121, 6607, (1999).
53. D. P. Curran, Z. Luo, and P. Degenkolb, Bioorg. Med. Chem. Lett., 8, 2403, (1998).
54. M. Larhed, M. Hoshino, S. Hadida, D. P. Curran, and A. Hallberg, J. Org. Chem., 62, 5583, (1997);
55. M. Hoshino, P. Degenkolb, and D. P. Curran, J. Org. Chem., 62, 8341, (1997).
56. J. Xiang, S. Toyoshima, A. Orita, and J. Otera, Angew. Chem. Int. Ed., 40, 3670, (2001);
57. A. Orita, Y. Hamada, T. Nakano, S. Toyoshima, and J. Otera, Chem. Eur. J., 7, 3321, (2001);
58. J. Xiang, A. Orita, and J. Otera, Adv. Synth. Cat., 344, 84, (2002).
59. E. Fouquet, A. Gabriel, B. Maillard, and M. Pereyre, Bull. Soc. Chim. Fr., 132, 590, (1995).
60. E. Fouquet, M. Pereyre, J.-C. Rayez, M.-T. Rayez, and T. Roulet, C. R. Acad. Sci. Paris, Chimie/Chem., 4, 641, (2001).
61. E. Fouquet, M. Pereyre, and A. L. Rodriguez, J. Org. Chem., 62, 5242, (1997);
62. A. Hervé, A. L. Rodriguez, and E. Fouquet, J. Org. Chem., 70, 1953, (2005).
63. A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356, (1993).
64. T. M. Cokley, R. L. Marshall, A. McCluskey, and D. J. Young, Tetrahedron Lett., 37, 1905, (1996);
65. T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961, (1997).
66. A. McCluskey, Green Chem., 1, 167, (1999).
67. Y. Z. Jin, N. Yasuda, H. Furuno, and J. Inanaga, Tetrahedron Lett., 44, 8765, (2003).
68. C. M. Gordon and A. McCluskey, Chem. Commun., 1431, (1999);
69. A. McCluskey, J. Garner, D. J. Young, and S. Caballero, Tetrahedron Lett., 41, 8147, (2000);
70. C. M. Gordon, and C. Ritchie, Green Chem., 4, 124, (2002).
71. S. T. Handy and X. Zhang, Org. Lett., 3, 233, (2001);
72. C. Chiappe, G. Imperato, E. Napolitano, and D. Pieraccini, Green Chem., 6, 33, (2004);
73. C. Chiappe, D. Pieraccini, D. Zhao, Z. Fei, and P. J. Dyson, Adv. Synth. Cat., 348, 38, (2006).
74. J. Vitz, D. H. Mac, and S. Legoupy, Green Chem., 9, 431, (2007);
75. J.-C. Poupon, D. Marcoux, J.-M. Cloarec, and A. B. Charette, Org. Lett., 9, 3591, (2007).
76. B. Delmond and G. Dumartin, in Solid State Organometallic Chemistry: Methods and Applications, M. Gielen, R. Willem, and B. Wrackmeyer (Eds), John Wiley & Sons, Ltd, Chichester, pp. 445-471, 1999.
77. H. Schumann and B. Pachaly, Angew. Chem. Int. Ed., 20, 1043, (1981).
78. Q. J. Fu, A. M. Steele, and S. C. Tsang, Green Chem., 3, 71, (2001);
79. S. A. Matlin and P. S. Gandham, Chem. Commun., 798, (1984).
80. D. C. Sherrington, Chem. Commun., 2275, (1998).
81. N. M. Weinshenker, G. A. Crosby, and J. Y. Wong, J. Org. Chem., 40, 1966, (1975).
82. J. R. Blanton and J. M. Salley, J. Org. Chem., 56, 490, (1991).
83. U. Gerigk, M. Gerlach, W. P. Neumann, R. Vieler, and V. Weintritt, Synthesis, 448, (1990);
84. J. R. Miller, and J.W. Hershberger, J. Polym. Sci., Polym. Lett., 25, 219, (1987);
85. W. P. Neumann and M. Peterseim, React. Polym., 20, 189, (1993).
86. H. Kuhn and W. P. Neumann, Synlett, 123, (1994).
87. J. Junggebauer and W. P. Neumann, Tetrahedron, 53, 1301, (1997).
88. G. Ruel, N. K. The, G. Dumartin, B. Delmond, and M. Pereyre, J. Organometal. Chem., 444, C18, (1993);
89. G. Dumartin, J. Kharboutli, B. Delmond, M. Pereyre, M. Biesemans, M. Gielen, and R.Willem, Organometallics, 15, 19, (1996).
90. G. Dumartin, G. Ruel, J. Kharboutli, B. Delmond, M.-F. Connil, B. Jousseaume, and M. Pereyre, Synlett, 952, (1994).
91. J.-M. Chrétien, A. Mallinger, F. Zammattio, E. Le Grognec, M. Paris, G. Montavon, and J.-P. Quintard, Tetrahedron Lett., 48, 1781, (2007).
92. J.-M. Chrétien, F. Zammattio, D. Gauthier, E. Le Grognec, M. Paris, and J.-P. Quintard, Chem. Eur. J., 12, 6816, (2006).
93. G. Kerric, J.-M. Chrétien, A. Tabatchnik-Rebillon, E. Le Grognec, F. Zammattio, and J.-P. Quintard, Abst 12th ICCOC-GTL, Galway, Ireland, p. 28, (2007).
94. C. Camacho-Camacho, M. Biesemans, M. Van Poeck, F. A. G. Mercier, R. Willem, K. Darriet-Jambert, B. Jousseaume, T. Toupance, U. Schneider, and U. Gerigk, Chem. Eur. J., 11, 2455, (2005).
95. G. Deshayes, K. Poelmans, I. Verbruggen, C. Camacho-Camacho, P. Degée, V. Pinoie, J. C. Martins, M. Piotto, M. Biesemans, R. Willem, and P. Dubois, Chem. Eur. J., 11, 4552, (2005).
96. K. Poelmans, V. Pinoie, I. Verbruggen, M. Biesemans, G. Van Assche, G. Deshayes, P. Degée, P. Dubois, and R. Willem, Appl. Organometal. Chem., 21, 504, (2007).
97. G. Ruel, G. Dumartin, B. Delmond, B. Lalère, O. F. X. Donard, and M. Pereyre, Appl. Organometal. Chem., 9, 591, (1995).
98. Y. Ueno, K. Chino, M. Watanabe, O. Moriya, and M. Okawara, J. Am. Chem. Soc., 104, 5564, (1982).
99. Q. Jiang, C. McDade, and A. W. Gross, US Patent 5436357 (1995) and US Patent 5561205 (1996).
100. A. Chemin, H. Deleuze, and B. Maillard, Eur. Polym. J., 34, 1395, (1998);
101. A. Mercier, H. Deleuze, B. Maillard, and O. Mondain-Monval, Adv. Synth. Cat., 344, 33, (2002).
102. D. H. Hunter and C. McRoberts, Organometallics, 18, 5577, (1999).
103. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, and M. Biesemans, Appl. Organometal. Chem., 19, 841, (2005);
104. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R.Willem, and M. Biesemans, J. Organometal. Chem., 691, 1965, (2006);
105. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R.Willem, and M. Biesemans, J. Organometal. Chem., 691, 3043, (2006).
106. A. Chemin, H. Deleuze, and B. Maillard, J. Chem. Soc., Perkin Trans. 1, 137, (1999).
107. A. Chemin, H. Deleuze, and B. Maillard, J. Appl. Polym. Sci., 79, 1297, (2001).
108. D. M. Whitfield and T. Ogawa, Glycoconjugate J., 15, 75, (1998).
109. A. G. Hernán, V. Guillot, A. Kuvshinov, and J. D. Kilburn, Tetrahedron Lett., 44, 8601, (2003).
110. A. G. Hernán and J. D. Kilburn, Tetrahedron Lett., 45, 831, (2004).
111. A. G. Hernán, P. N. Horton, M. B. Hursthouse, and J. D. Kilburn, J. Organometal. Chem., 691, 1466, (2006).
112. X. Zhu, B. E. Blough, and F. I. Carroll, Tetrahedron Lett., 41, 9219, (2000).
113. K. C. Nicolaou, N. Winssinger, J. Pastor, and F. Murphy, Angew. Chem. Int. Ed., 37, 2534, (1998).
114. J. Cossy, C. Rasamison, and D. Gomez Pardo, J. Org. Chem., 66, 7195, (2001).
115. J. Cossy, C. Rasamison, D. Gomez Pardo, and J. A. Marshall, Synlett, 629, (2001).
116. J. Cossy, M. Defosseux, and C. Meyer, Synlett, 815, (2001).
117. S. Bräse, J. H. Kirchhoff, and J. Köbberling, Tetrahedron, 59, 885, (2003).
118. E. J. Enholm, M. E. Gallagher, K. M. Moran, J. S. Lombardi, and J. P. Schulte, II., Org. Lett., 1, 689, (1999).
119. E. J. Enholm and J. P. Schulte, II., Org. Lett., 1, 1275, (1999).
120. S. Thibaud, L. Moine, M. Degueil, and B. Maillard, Eur. Polym. J., 42, 1273, (2006).
121. L. Angiolini, M. Biesemans, D. Caretti, E. Salatelli, and R.Willem, Polymer, 42, 3913, (2000);
122. H. Dalil, M. Biesemans, R. Willem, L. Angiolini, E. Salatelli, D. Caretti, N. A. Chaniotakis, and K. Perdikaki, Helv. Chim. Acta, 85, 852, (2002);
123. L. Angiolini, E. Salatelli, D. Caretti, M. Biesemans, H. Dalil, R. Willem, N. A. Chaniotakis, E. Gouliaditi, and K. Perdikaki, Macromol. Chem. Phys., 203, 219, (2002);
124. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, and M. Biesemans, J. Polym. Sci. Part A: Polym. Chem., 42, 5372, (2004).
125. L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, and M. Biesemans, J. Polym. Sci. Part A: Polym. Chem., 43, 3091, (2005);
126. D. Tonelli, I. Carpani, L. Mazzocchetti, L. Angiolini, D. Caretti, E. Salatelli, and F. Tarterini, Electronalysis, 18, 1055, (2006).
127. G. Dumartin, M. Pourcel, B. Delmond, O. Donard, and M. Pereyre, Tetrahedron Lett., 39, 4663, (1998).
128. M. Pourcel, PhD. Thesis, University of Bordeaux 1 (France), 1997.
129. M. Gerlach, F. Jördens, H. Kuhn, W. P. Neumann, and M. Peterseim, J. Org. Chem., 56, 5971, (1991).
130. W. P. Neumann, J. Organometal. Chem., 437, 23, (1992).
131. W. P. Neumann and M. Peterseim, Synlett, 801, (1992).
132. P. Boussaget, B. Delmond, G. Dumartin, and M. Pereyre, Tetrahedron Lett., 41, 3377, (2000).
133. C. Bokelmann, W. P. Neumann, and M. Peterseim, J. Chem. Soc., Perkin Trans. 1, 3165, (1992).
134. D. P. Dygutsch, W. P. Neumann, and M. Peterseim, Synlett, 363, (1994).
135. A. Chemin, A. Mercier, H. Deleuze, B. Maillard, and O. Mondain-Monval, J. Chem. Soc., Perkin Trans. 1, 366, (2001).
136. J. Junggebauer and W. P. Neumann, Tetrahedron, 53, 1301, (1997).
137. M. Harendza, K. Leßmann, and W. P. Neumann, Synlett, 283, (1993).
138. W. M. Macindoe, A. Williams, and R. Khan, Carbohydr. Res., 283, 17, (1996).
139. F. A. G. Mercier, M. Biesemans, R. Altmann, R. Willem, R. Pintelon, J. Schoukens, B. Delmond, and G. Dumartin, Organometallics, 20, 958, (2001).
140. J. C. Martins, F. A. G. Mercier, A. Vandervelden, M. Biesemans, J.-M. Wieruszeski, E. Humpfer, R. Willem, and G. Lippens, Chem. Eur. J., 8, 3431, (2002).
141. M. Biesemans, F. A. G. Mercier,M. Van Poeck, J. C. Martins, G. Dumartin, and R.Willem, Eur. J. Inorg. Chem., 2908, (2004).
142. J.-M. Chrétien, F. Zammattio, E. Le Grognec, M. Paris, B. Cahingt, G. Montavon, and J.-P. Quintard, J. Org. Chem., 70, 2870, (2005).
143. G. Dumartin, J. Kharboutli, B. Delmond, Y. Frangin, and M. Pereyre, Eur. J. Org. Chem., 781, (1999).
144. G.W. Kabalka, M. M. Goodman, R. S. Srivastava,K.R.Bowers, and R. C. Marks, J. Label. Compd. Radiopharm., 35, 220, (1994).
145. E. Berthommier, S. Chalon, B. Delmond, G. Dumartin, F. Marchi, L. Mauclaire, and M. Pereyre, J. Label. Compd. Radiopharm., 40, 96, (1997).
146. P. A. Culbert and D. H. Hunter, React. Polym., 19, 247, (1993);
147. D. H. Hunter, A.M. Marinesch, C. Loc'h, and B. Mazière, J. Label. Compd. Radiopharm., 37, 144, (1995).