Silylboranes as new sources of silyl radicals for chain-transfer reactions

Chemistry - A European Journal

Volumn 18, Issue 3, 2012, Pages 940-950

  Rouquet, Guy ^a   Robert, Frédéric ^a   Méreau, Raphaãl ^a   Castet, Frédéric ^a   Renaud, Philippe ^b   Landais, Yannick ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

gem dialkyl effect; homolytic substitution; hydroboration; hydrogen transfer; radical reactions

Indexed keywords

GEM-DIALKYL EFFECT; HOMOLYTIC SUBSTITUTION; HYDROBORATION; HYDROGEN TRANSFER; RADICAL REACTIONS;

CYCLIZATION; HYDROGEN; REACTION KINETICS;

SILICON;

EID: 84855664209     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102318     Document Type: Article

References (124)

1. M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987.
2. G. Batley, in Tributyltin: Case Study of an Environmental Contaminant (Ed.:, S. J. de Mora,), Cambridge University Press, Cambridge, 1996, p. 139
3. E. A. Clark, R. M. Sterritt, J. N. Lester, Environ. Sci. Technol. 1988, 22, 600
4. R. B. Laughlin Jr., in Organotin: Environmental Fate and Effects (Eds.:, M. A. Champ, P. F. Seligman,), Chapman and Hall, London, 1996, p. 331
5. M. J. F. Leroy, P. Quevauviller, O. Donard, M. Astruc, Pure Appl. Chem. 1998, 70, 2051
6. R. J. Maguire, Water Qual. Res. J. Can. 2000, 35, 633
7. L. Viglino, E. Pelletier, R. St-Louis, Environ. Toxicol. Chem. 2004, 23, 2673.
8. G. Dumartin, M. Pourcel, B. Delmond, O. Donard, M. Pereyre, Tetrahedron Lett. 1998, 39, 4663
9. K. Hayashi, J. Iyoda, I. Shiihara, J. Organomet. Chem. 1967, 10, 81
10. E. J. Corey, J. W. Suggs, J. Org. Chem. 1975, 40, 2554
11. M. Gerlach, F. Jordens, H. Kuhn, W. P. Neumann, M. Peterseim, J. Org. Chem. 1991, 56, 5971
12. S. Thibaud, L. Moine, M. Degueil, B. Maillard, Eur. Polym. J. 2006, 42, 1273
13. D. P. Curran, S. Halida, J. Am. Chem. Soc. 1996, 118, 2531
14. J. Light, R. Breslow, Tetrahedron Lett. 1990, 31, 2957
15. D. L. J. Clive, J. Wang, J. Org. Chem. 2002, 67, 1192
16. G. Stork, P. M. Sher, J. Am. Chem. Soc. 1986, 108, 303
17. J. M. Berge, S. M. Roberts, Synthesis 1979, 471
18. P. Renaud, E. LacÃ?te, L. Quaranta, Tetrahedron Lett. 1998, 39, 2123
19. D. C. Harrowven, D. P. Curran, S. L. Kostiuk, I. L. Wallis-Guy, S. Whiting, K. J. Stenning, B. Tang, E. Packard, L. Nanson, Chem. Commun. 2010, 46, 6335.
20. P. A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272
21. Angew. Chem. Int. Ed. 1998, 37, 3072
22. A. Studer, S. Amrein, Synthesis 2002, 835
23. G. J. Rowlands, Tetrahedron 2009, 65, 8603
24. Radicals in Organic Synthesis, Vols. 1-2 (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001.
25. C. Chatgilialoglu, Organosilanes in Radical Chemistry, Wiley, Chichester, 2004
26. C. Chatgilialoglu, Acc. Chem. Res. 1992, 25, 188.
27. R. Walsh, Acc. Chem. Res. 1981, 14, 246
28. M. F. Lappert, J. B. Pedley, J. Simpson, T. R. Spalding, J. Organomet. Chem. 1971, 29, 195
29. B. C. Gilbert, A. F. Parsons, J. Chem. Soc. Perkin Trans. 2 2002, 367.
30. C. Chatgilialoglu, M. Ballestri, D. Vecchi, D. P. Curran, Tetrahedron Lett. 1996, 37, 6383
31. C. Chatgilialoglu, C. Ferreri, M. Ballestri, D. P. Curran, Tetrahedron Lett. 1996, 37, 6387
32. K. Miura, H. Saito, T. Nakagawa, T. Hondo, J. Tateiwa, M. Sonoda, A. Hosomi, J. Org. Chem. 1998, 63, 5740.
33. B. P. Roberts, Chem. Soc. Rev. 1999, 28, 25
34. S. J. Cole, J. N. Kirwan, B. P. Roberts, C. R. Willis, J. Chem. Soc. Perkin Trans. 1 1991, 103
35. H.-S. Dang, M. R. J. Elsegood, K.-M. Kim, B. P. Roberts, J. Chem. Soc. Perkin Trans. 1 1999, 2061.
36. A. Studer, S. Amrein, Angew. Chem. 2000, 112, 3196
37. Angew. Chem. Int. Ed. 2000, 39, 3080
38. A. Studer, S. Amrein, F. Schleth, T. Schulte, J. C. Walton, J. Am. Chem. Soc. 2003, 125, 5726
39. J. C. Walton, A. Studer, Acc. Chem. Res. 2005, 38, 794.
40. H. Sakurai, A. Hosomi, J. Am. Chem. Soc. 1971, 93, 1709
41. C. Chatgilialoglu, K. U. Ingold, J. C. Scaiano, J. Am. Chem. Soc. 1983, 105, 3292
42. A. Matsumoto, Y. Ito, J. Org. Chem. 2000, 65, 5707
43. S. M. Horvat, C. H. Schiesser, L. M. Wild, Organometallics 2000, 19, 1239
44. Z. Zhu, C. Wang, X. Xiang, C. Pi, X. Zhou, Chem. Commun. 2006, 2066
45. J. W. Wilt, W. K. Chwang, J. Am. Chem. Soc. 1974, 96, 6194
46. J. W. Wilt, C. F. Dockus, J. Am. Chem. Soc. 1970, 92, 5813
47. J. W. Wilt, W. K. Chwang, C. F. Dockus, N. M. Tomiuk, J. Am. Chem. Soc. 1978, 100, 5534
48. S. Kim, C. J. Lim, C. Song, W.-J. Chung, J. Am. Chem. Soc. 2002, 124, 14306
49. S. Kim, C. J. Lim, Angew. Chem. 2004, 116, 5492
50. Angew. Chem. Int. Ed. 2004, 43, 5378
51. J. Y. Lee, Y. T. Hong, S. Kim, Angew. Chem. 2006, 118, 6328
52. Angew. Chem. Int. Ed. 2006, 45, 6182
53. G. Pandey, S. R. Gadre, Acc. Chem. Res. 2004, 37, 201
54. S. E. Vaillard, C. Mück-Lichtenfeld, S. Grimme, A. Studer, Angew. Chem. 2007, 119, 6653
55. Angew. Chem. Int. Ed. 2007, 46, 6533
56. M. C. Lamas, A. Studer, Org. Lett. 2011, 13, 2236.
57. K. Shiina, M. Kumada, J. Org. Chem. 1958, 23, 139
58. H. Sakurai, R. Koh, A. Hosomi, M. Kumada, Bull. Chem. Soc. Jpn. 1966, 39, 2050
59. K. J. Kulicke, C. Chatgilialoglu, B. Kopping, B. Giese, Helv. Chim. Acta 1992, 75, 935
60. K. Miura, K. Oshima, K. Utimoto, Chem. Lett. 1992, 2477
61. K. Miura, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1993, 66, 2348
62. C. Chatgilialoglu, Chem. Rev. 1995, 95, 1229
63. A. Studer, Angew. Chem. 1998, 110, 507
64. Angew. Chem. Int. Ed. 1998, 37, 462
65. A. Studer, H. Steen, Chem. Eur. J. 1999, 5, 759
66. S. Amrein, M. Bossart, T. Vasella, A. Studer, J. Org. Chem. 2000, 65, 4281.
67. D. P. Curran, J. Xu, E. Lazzarini, J. Am. Chem. Soc. 1995, 117, 6603
68. D. Clive, M. Contin, J. Chem. Soc. Chem. Commun. 1995, 319.
69. C. H. Schiesser, Chem. Commun. 2006, 4055
70. C. H. Schiesser, L. M. Wild, Tetrahedron 1996, 52, 13265
71. H. Matsubara, C. H. Schiesser, J. Org. Chem. 2003, 68, 9299
72. A. Studer, S. Amrein, H. Matsubara, C. H. Schiesser, T. Doi, T. Kawamura, T. Fukuyama, I. Ryu, Chem. Commun. 2003, 1190.
73. C. Chatgilialoglu, A. Guarini, A. Guerrini, G. Seconi, J. Org. Chem. 1992, 57, 2207
74. A. I. Prokof'ev, T. I. Prokof'eva, I. S. Belostotskaya, N. N. Bubnov, S. P. Solodovnikov, V. V. Ershov, M. I. Kabachnik, Tetrahedron 1979, 35, 2471
75. A. Alberti, A. Hudson, Chem. Phys. Lett. 1977, 48, 331
76. A. Alberti, C. Chatgilialoglu, Tetrahedron 1990, 46, 3963
77. S. Kim, J. Y. Doo, K. M. Lim, J. Chem. Soc. Perkin Trans. 1 1994, 2517.
78. V. Darmency, P. Renaud, Top. Curr. Chem. 2006, 263, 71-106; for earlier studies, see
79. A. Suzuki, A. Arase, H. Matsumoto, M. Itoh, H. C. Brown, M. M. Rogic, M. W. Rathke, J. Am. Chem. Soc. 1967, 89, 5708
80. G. W. Kabalka, H. C. Brown, A. Suzuki, S. Honma, A. Arase, M. Itoh, J. Am. Chem. Soc. 1970, 92, 710.
81. A.-P. Schaffner, P. Renaud, Angew. Chem. 2003, 115, 2762
82. Angew. Chem. Int. Ed. 2003, 42, 2658
83. E. Godineau, C. Schäfer, Y. Landais, Org. Lett. 2006, 8, 4871
84. E. Godineau, Y. Landais, J. Am. Chem. Soc. 2007, 129, 12662.
85. C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695.
86. C. E. Garrett, G. C. Fu, J. Org. Chem. 1996, 61, 3224.
87. F. Bertrand, F. Le Guyader, L. Liguori, G. Ouvry, B. Quiclet-Sire, S. Seguin, S. Z. Zard, C. R. Acad. Sci. Ser. IIc: Chim. 2001, 4, 547
88. A.-P. Schaffner, V. Darmency, P. Renaud, Angew. Chem. 2006, 118, 5979
89. Angew. Chem. Int. Ed. 2006, 45, 5847
90. S. Kim, S. Kim, Bull. Chem. Soc. Jpn. 2007, 80, 809.
91. S. Kim, I. Y. Lee, J.-Y. Yong, D. H. Oh, J. Am. Chem. Soc. 1996, 118, 5138.
92. M. Kobayashi, K. Tanaka, H. Minato, Bull. Chem. Soc. Jpn. 1972, 45, 2906
93. C. M. M. da Silva Correa, A. S. Lindsay, W. A. Waters, J. Chem. Soc. C 1968, 1872.
94. 2BCat, see:, A. Kapat, A. König, F. Montermini, P. Renaud, J. Am. Chem. Soc. 2011, 133, 13890.
95. A.-P. Schaffner, F. Montermini, D. Pozzi, V. Darmency, E. M. Scanlan, P. Renaud, Adv. Synth. Catal. 2008, 350, 1163.
96. M. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735; for reports on the use of gem-dialkyl effect in radical cyclizations, see
97. M. E. Jung, I. D. Trifunovich, N. Lensen, Tetrahedron Lett. 1992, 33, 6719
98. M. E. Jung, M. Kiankarimi, J. Org. Chem. 1995, 60, 7013
99. M. E. Jung, R. Marquez, Tetrahedron Lett. 1997, 38, 6521
100. M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968
101. M. E. Jung, R. Marquez, K. N. Houk, Tetrahedron Lett. 1999, 40, 2661
102. M. E. Jung, Synlett 1999, 843
103. H. O. House, P. D. Weeks, J. Am. Chem. Soc. 1975, 97, 2778
104. A. L. J. Beckwith, T. Lawrence, J. Chem. Soc. Perkin Trans. 2 1979, 1535
105. A. L. J. Beckwith, C. J. Easton, T. Lawrence, A. K. Serelis, Aust. J. Chem. 1983, 36, 545
106. A. L. J. Beckwith, C. H. Schiesser, Tetrahedron 1985, 41, 3925
107. A. L. J. Beckwith, C. H. Schiesser, Tetrahedron Lett. 1985, 26, 373
108. E. W. Della, P. A. Smith, Tetrahedron Lett. 2001, 42, 481
109. G. A. Russell, C. Li, P. Chen, J. Am. Chem. Soc. 1996, 118, 9831
110. C. Wang, G. A. Russell, J. Org. Chem. 1999, 64, 2066
111. B. Delouvrié, L. Fensterbank, E. LacÃ?te, M. Malacria, J. Am. Chem. Soc. 1999, 121, 11305.
112. G. Povie, G. Villa, L. Ford, D. Pozzi, C. H. Schiesser, P. Renaud, Chem. Commun. 2010, 46, 803
113. D. Pozzi, E. Scanlan, P. Renaud, J. Am. Chem. Soc. 2005, 127, 14204
114. G. Villa, G. Povie, P. Renaud, J. Am. Chem. Soc. 2011, 133, 5913.
115. P. C. Wong, P. R. Marriott, D. Griller, D. C. Nonhebel, M. J. Perkins, J. Am. Chem. Soc. 1981, 103, 7761.
116. M. Newcomb, Tetrahedron 1993, 49, 1151
117. M. Newcomb, in Radicals in Organic Synthesis, Vol. 1 (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001, p. 317.
118. R. F. Brown, N. M. Van Gulick, J. Org. Chem. 1956, 21, 1046.
119. R. Méreau, P. d'Antuono, F. Castet, G. Rouquet, F. Robert, Y. Landais, Organometallics 2010, 29, 2406.
120. H. Zipse, Top. Curr. Chem. 2006, 263, 163
121. J. Hioe, H. Zipse, Org. Biomol. Chem. 2010, 8, 3609.
122. G. D. Mendenhall, Tetrahedron Lett. 1983, 24, 451
123. J. T. Banks, J. C. Scaiano, W. Adams, R. S. Oestrich, J. Am. Chem. Soc. 1993, 115, 2473.
124. Gaussian 09, Revision A02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.