Metal-catalyzed hydrostannations

Chemical Reviews

Volumn 100, Issue 8, 2000, Pages 3257-3282

  Smith, Nicholas D ^b   Mancuso, John ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; FREE RADICALS; MOLECULAR STRUCTURE; MOLECULES; REACTION KINETICS; STOICHIOMETRY; TRANSITION METALS;

HYDROSTANNATIONS; ORGANOSTANNANES; PROTONATION; STANNYLMETALATION;

ORGANOMETALLICS;

EID: 0034249725     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9902695     Document Type: Article

References (93)

1. Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
2. Davies, A. G. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 2, p 217.
3. (a) Omae, I. Organotin Chemistry, Journal of Organometallic Chemistry Library; Elsevier: Amsterdam, 1989; Vol. 21. Neumann, W. P. The Organic Chemistry of Tin; J. Wiley: New York, 1970.
4. (a) Omae, I. Organotin Chemistry, Journal of Organometallic Chemistry Library; Elsevier: Amsterdam, 1989; Vol. 21. Neumann, W. P. The Organic Chemistry of Tin; J. Wiley: New York, 1970.
5. (b) Nativi, C.; Taddei, M. J. Org. Chem. 1988, 53, 820.
6. (c) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 705, 2547.
7. (d) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982, 47, 404. Jung, M. E.; Light, L. A. Tetrahedron Lett. 1982, 23, 3851.
8. (d) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982, 47, 404. Jung, M. E.; Light, L. A. Tetrahedron Lett. 1982, 23, 3851.
9. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. J Chem Soc., Chem. Commun. 1993, 9, 788.
10. (a) Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178.
11. (b) Nakamura, E.; Machii, D.; Inubushi, T. J. J. Am. Chem. Soc. 1989, 111, 6849.
12. Piers, E.; Chong, J. M. J. Chem Soc., Chem Commun. 1983, 934.
13. (a) Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzalez, A. M.; Pulido, F. J. J. Chem. Soc., Perkin I 1992, 351.
14. (b) Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163.
15. (c) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768.
16. (a) Hibino, J.; Matsubara, S.; Morizawa, Y. Oshima, K. Tetrahedron Lett. 1984, 25, 2151.
17. (b) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K. J. Organomet. Chem. 1985, 285, 163.
18. (c) Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163.
19. (d) Nonaka, T.; Okuda, Y.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1986, 51, 4716.
20. (a) Piers, E.; Skerlj, R. T. J. Chem Soc., Chem. Commun. 1986, 626.
21. (b) Mitchell, T. N.; Amamaria, A.; Killing, H.; Rutchow, D. J. Organomet. Chem. 1986, 304, 257.
22. (c) Beaudet, I.; Parrain, J.-L.; Quintard, J.-L. Tetrahedron Lett. 1991, 32, 6333.
23. (d) Murakami, M.; Amii, H.; Takizawa, N.; Ito, Y. Organometallics 1993, 12, 4223.
24. (e) Mabon, R.; Richecoeur, A. M. E.; Sweeney, J. B. J. Org. Chem. 1999, 64, 328.
25. Nozaki, K.; Wakamatsu, K.; Nonaka, T.; Tuckmantel, W.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1986, 27, 2007.
26. Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064.
27. Sharma, S.; Oehlschlager, A. C. Tetrahedron Lett. 1986, 27, 6161.
28. Casson, S.; Kocienski, P. J. In Organometallic Reagents in Organic Synthesis; Academic Press: 1994; p 129.
29. Casachi, A.; Grigg, R.; Sansano, J. M.; Wilson, D.; Redpath, J. Tetrahedron Lett. 1996, 37, 4413.
30. Trost, B. M.; Li, C. J. Synthesis 1994, 1267.
31. Liron, F.; Le Garrec, P.; Alami, M. Synlett 1999, 2, 246.
32. (a) LautensM.; Kumanovic S.; Meyer C. Angew. Chem., Int. Ed. Engl. 1996, 1329.
33. (b) Lautens, M.; Smith, N. D.; Ostrovsky, D. J. Org. Chem. 1997, 62, 8970.
34. (a) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
35. (b) Kazmaier, U.; Schauss, D, Pohlman, M. Org. Lett. 1999, 1, 7, 1017.
36. Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem Lett. 1988, 881.
37. Bamba, M.; Nishikawa, T.; Isobe, M. Tetrahedron Lett. 1996, 37, 45, 8199.
38. Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetrahedron Lett. 1990, 6621.
39. Maleczka, R. E.; Terrell, L. R.; Clark, D. H.; Whitehead S. L.; Gallagher, W. P.; Tersteige, I. J. Org. Chem. 1999, 64, 5958.
40. Greeves, N.; Torode, J. S.; Synlett 1994, 537.
41. Matsukawa, Y.; Asao, N.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 3779.
42. Gevorgyan, V.; Liu, J. X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963.
43. Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676.
44. Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
45. Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981.
46. (a) Asao, N.; Liu, J. X.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405-2406.
47. (b) Asao, N.; Liu, J. X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568.
48. Barbero, A.; Cuadradro, P.; Fleming, I.; Gonzalez, A. M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351.
49. Cochran, J. C.; Phillips, H. K.; Tom, S.; Hurd, A. R.; Bronk, B. S. Organometallics 1994, 13, 947.
50. Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
51. Crisp, G. T.; Gebauer, M. G. J. Organomet. Chem. 1997, 532, 83.
52. Maleczka, R. E.; Gallagher, W. P.; Terstiege, I. J. Am. Chem. Soc. 2000, 122, 384.
53. Smith, A. B.; Ott, G. R. J. Am. Chem. Soc. 1998, 120, 3935.
54. Jarosz, S.; Kozlowska, E. Pol. J. Chem. 1994, 68, 539.
55. Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617.
56. Lipshutz, B. H.; Ellsworth, E. L.; Dimmock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065.
57. Betzer, J.-F.; Lallemand, J.-Y.; Pancrazi, A. Synthesis 1998, 522.
58. Oikawa, H.; Yoneta, Y.; Ueno, T.; Oikawa, M.; Wakayama, W.; Ichihara, A. Tetrahedron Lett. 1997, 38, 7897-7900.
59. Semmelhack, M. F.; Epa, W. R.; Cheung, A. W-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455-7456.
60. Rossi, R.; Carpita, A.; Cossi, P. Tetrahedron Lett. 1992, 33, 4495-4498.
61. Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetrahedron Lett. 1990, 31, 6621-6624.
62. Rossi, R.; Carpita, A.; Cossi, P. Synth. Commun. 1993, 23, 143-152.
63. Sai, H.; Ogiku, T.; Nishitani, T.; Hiramatsu, H.; Horikawa, H.; Iwasaki, T. Synthesis 1995, 582-586.
64. Gracia, J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1998, 2865-2871.
65. Thibonnet, J.; Launay, V.; Abarbi, M.; Duchêne, A.; Parrain J.-L. Tetrahedron Lett. 1998, 39, 4277-4280.
66. Labadie, J. W.; Teuting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634.
67. Alami, M. Ferri, F. Synlett 1996, 755.
68. Ferri, F.; Alami, M. Tetrahedron Lett. 1996, 37, 7971.
69. Lautens, M.; Mancuso, J. Org. Lett. 2000, 2, 671.
70. Lautens, M.; Smith, N.; Ostrovsky, D. Unpublished work.
71. Markl, G.; Kniedl, F. Angew. Chem., Int. Ed. Engl. 1973, 12, 931.
72. Casson, S.; Kocienski, P. Synthesis 1993, 1133.
73. Magriotis, P. A.; Brown, J. T.; Scott, M. E. Tetrahedron Lett. 1991, 32, 5047.
74. Pimm, A.; Kocienski, P.; Street, S. D. A. Synlett 1992, 886.
75. Paley, R. S.; Weers, H. L.; Fernandez, P. Tetrahedron Lett. 1995, 36, 21, 3605.
76. Huang, X.; Ma, Y. Synth. Commun. 1997, 27, 2407.
77. Magriotis, P. A.; Doyle, T. J.; Kim, K. D. Tetrahedron Lett. 1990, 31, 2541.
78. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 1 1996, 20, 2417.
79. Keinan, E. Gleize, P. A. Tetrahedron Lett. 1982, 23, 477.
80. Four, P.; Guibe, F. Tetrahedron Lett. 1982, 23, 1825.
81. Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 770.
82. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K.; J. Chem. Soc., Chem. Commun. 1993, 9, 788.
83. Plamondon, L.; Wuest, J. D. J. Org. Chem. 1991, 56, 2076.
84. Smadja, W.; Zahouily, M.; Malacria, M. Tetrahedron Lett. 1992, 38, 5511.
85. Miyake, H. Yamamura, K. Chem Lett. 1992, 507.
86. Miyake, H. Yamamura, K. Chem Lett. 1992, 1099.
87. Voskoboynikov, A. Z.; Beletskaya, I. P. New J. Chem. 1995, 19, 723.
88. Lautens, M.; Klute W. Angew. Chem., Int. Ed. Engl. 1996, 35, 442.
89. Ichinose, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1988, 61, 2693.
90. Mitchell, T. N.; Schneider, U. J. Organomet. Chem. 1991, 405, 195.
91. Koerber, K.; Goré, J.; Vatele, J. M. Tetrahedron Lett. 1991, 32, 1187.
92. Grigg, R.; Sansano, J. M.Tetrahedron Lett. 1996, 52, 13441.
93. Lautens, M.; Ostrovsky, D.; Tao, B. Tetrahedron Lett. 1997, 38, 6343.