Angewandte
Chemie
À
[36] C.-F. Yao, C.-M. Chu, J.-T. Liu, J. Org. Chem. 1998, 63, 719.
Keywords: C C coupling · hydroboration · olefination ·
radical reactions · sulfones
.
[37] C. E. Garett, G. C. Fu, J. Org. Chem. 1996, 61, 3224.
[38] R. F. W. Jackson, S. P. Standen, W. Clegg, A. McCamley, J. Chem.
Soc. Perkin Trans. 1 1995, 141.
[39] a) S. Kim, I. Y. Lee, J.-Y. Yoon, D. H. Oh, J. Am. Chem. Soc.
1996, 5138;b) S. Kim, C. J. Lim, Bull. Korean Chem. Soc. 2003,
24, 1219.
[40] G. A. Russell, P. Ngoviwatchai, Tetrahedron Lett. 1986, 27, 3479.
[41] J. C. Gong, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 4486.
[42] Coupling with a reverse polarity of the reagents (Sonogashira
and Kumada–Corriu reactions), involving electrophilic alkyl
halides with alkynyl nucleophiles are known: M. Eckhardt, G. C.
Fu, J. Am. Chem. Soc. 2003, 125, 13642; L. M. Yang, L.-F.
Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461.
[43] A procedure for the preparation of acetylene derivatives from
organoboranes through iodine-mediated rearrangement of ate
complexes has been reported: H. C. Brown, V. K. Mahindroo,
N. G. Bhat, B. Singaram, J. Org. Chem. 1991, 56, 1500.
[44] For a review on acetylenic sulfones, see: T. G. Back, Tetrahedron
2001, 57, 5263.
[45] Alkynylation with alkynyl phenyl sulfones such as non-1-ynyl
phenyl sulfone and 3-methylbut-1-ynyl phenyl sulfone do not
afford the desired products, because simple aliphatic chains are
not able to orient the radical addition at the a-position of the
sulfonyl group. However, such products are available from the
reaction with the Me3Si-substituted reagent 21, followed by
desilylation and by alkylation of the terminal acetylene deriv-
ative.
[46] Radical-mediated decarboxylative cyanation using tosyl cyanide
has been reported: D. H. R. Barton, J. C. Jaszberenyi, E. A.
Theodorakis, Tetrahedron 1992, 48, 2613.
[47] J.-M. Fang, M.-Y. Chen, Tetrahedron Lett. 1987, 28, 2853.
[48] S. Kim, H.-J. Song, Synlett 2002, 2110.
[1] H. C. Brown, Angew. Chem. 1980, 92, 675.
[2] H. C. Brown, Boranes in Organic Chemistry, Cornell University
Press, Ithaca, 1972.
[3] H. C. Brown, G. W. Kramer, A. B. Levy, M. M. Midland,
Organic Synthesis via Boranes, Wiley, New York, 1975.
[4] H. C. Brown, Hydroboration, Benjamin-Cumming, Reading,
1980.
[5] A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic
Press, London, 1988.
[6] D. S. Matteson, Stereodirected Synthesis with Organoboranes,
Springer, Berlin, 1995.
[7] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
[8] For reviews on organoboron compounds, see: N. Miyaura, Cross-
Coupling Reactions: A Practical Guide, Vol. 219, Springer,
Berlin, 2002.
[9] F. Bellina, R. Rossi, Synthesis 2004, 2419.
[10] H. C. Brown, M. M. Midland, Angew. Chem. 1972, 84, 702;
Angew. Chem. Int. Ed. Engl. 1972, 11, 692.
[11] B. Giese, Radicals in Organic Syntheses: Formation of Carbon-
Carbon Bonds, Pergamon, Oxford, 1986.
[12] C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415.
[13] A.-P. Schaffner, P. Renaud, Eur. J. Org. Chem. 2004, 2291.
[14] V. Darmency, P. Renaud in Topics in Current Chemistry, Vol. 263
(Ed.: A. Gansaeuer), Springer, Berlin, 2006, p. 71.
[15] A.-P. Schaffner, P. Renaud, Angew. Chem. 2003, 115, 2762;
Angew. Chem. Int. Ed. 2003, 42, 2658.
[16] A.-P. Schaffner, B. Becattini, C. Ollivier, V. Weber, P. Renaud,
Synthesis 2003, 2740.
[17] V. Darmency, E. M. Scanlan, A.-P. Schaffner, P. Renaud, Org.
Synth. 2005, 83, 24.
[49] B. Becattini, C. Ollivier, P. Renaud, Synlett 2003, 1485.
[18] V. Darmency, P. Renaud, Chimia 2005, 59, 109.
[19] F. Bertrand, F. Le Guyader, L. Liguori, G. Ouvry, B. Quiclet-
Sire, S. Seguin, S. Z. Zard, C. R. Acad. Sci. Ser. II C 2001, 4, 547.
[20] G. A. Russell, P. Ngoviwatchai, H. I. Tashtoush, A. Pladalmau,
R. K. Khanna, J. Am. Chem. Soc. 1988, 110, 3530.
[21] G. A. Russell, P. Ngoviwatchai, J. Org. Chem. 1989, 54, 1836.
[22] N. Ono, A. Kamimura, A. Kaji, J. Org. Chem. 1987, 52, 5111.
[23] A. J. Clark, S. Rooke, T. J. Sparey, P. C. Taylor, Tetrahedron Lett.
1996, 37, 909.
[24] Recently, the first example of the introducion of a trimethylsi-
lylethynyl group was reported: S. Usugi, H. Yorimitsu, H.
Shinokubo, K. Oshima, Bull. Chem. Soc. Jpn. 2002, 75, 2687.
[25] K. Takami, S. I. Usugi, H. Yorimitsu, K. Oshima, Synthesis 2005,
824.
[26] K. Takami, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4555.
[27] For a review on radical fragmentation processes, see: I. J.
Rosenstein in Radicals in Organic Synthesis, Vol. 1 (Eds.: P.
Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, p. 50.
[28] J. Xiang, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 11986.
[29] J. Xiang, W. Jiang, J. Gong, P. L. Fuchs, J. Am. Chem. Soc. 1997,
119, 4123.
[30] F. Bertrand, B. Quiclet-Sire, S. Z. Zard, Angew. Chem. 1999, 111,
2135; Angew. Chem. Int. Ed. 1999, 38, 1943.
[31] D. Leca, L. Fensterbank, E. Lacꢀte, M. Malacria, Angew. Chem.
2004, 116, 4316; Angew. Chem. Int. Ed. 2004, 43, 4220.
[32] D. Leca, K. Song, M. Albert, M. G. Goncalves, L. Fensterbank,
E. Lacꢀte, M. Malacria, Synthesis 2005, 1405.
[33] B. Delouvriꢁ, L. Fensterbank, E. Lacꢀte, M. Malacria, J. Am.
Chem. Soc. 1999, 121, 11395.
[34] N. Miyamoto, D. Fukuoka, K. Utimoto, H. Nozaki, Bull. Soc.
Chem. Jpn. 1974, 47, 503.
[35] J.-T. Liu, Y.-J. Jang, Y.-K. Shih, S.-R. Hu, C.-M. Chu, C.-F. Yao, J.
Org. Chem. 2001, 66, 6021.
Angew. Chem. Int. Ed. 2006, 45, 5847 –5849
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim