New type formation of 1,3-enynes (or internal alkynes) via coupling of organoboranes with alkynylcopper compounds mediated by copper(II)

Abstract

The copper(II)—mediated coupling reaction of alkenyldialkyl- or trialkyl-boranes with alkynylcopper compounds (generated in situ), in the presence of appropriate solvents and a small amount of water, gives (E)-1,3-enynes (or disubstituted alkynes) with various functional groups in reasonable yields.

References

1. Review: J. F. Normant and A. Alexakis, Synthesis, 1981, 841.
2. For example: E. J. Corey and A. Tramontano, J. Am. Chem. Soc., 1984, 106, 462; P. J. Stang and T. Kitamura, J. Am. Chem. Soc., 1987, 109, 7561; M. M. Salter, V. Gevorgyan, S. Saito and Y. Yamamoto, Chem. Commun., 1996, 17; S. Saito, M. M. Salter, V. Gevorgyan, N. Tsuboya, K. Tando and Y. Yamamoto, J. Am. Chem. Soc., 1996, 118, 3970.
3. For more recent example: P. Ramiandrasoa, B. Bréhon, A. Thivet, M. Alami and G. Cahiez, Tetrahedron Lett., 1997, 38, 2447; R. Hara, Y. Liu, W.-H. Sun and T. Takahashi, Tetrahedron Lett., 1997, 38, 4103.
4. G. Pattenden, in Comprehensive Organic Chemistry, ed. J. F. Stoddart, Pergamon, Oxford, 1979, vol. 1, p. 171; R. C. Larock, in Comprehensive Organic Transformations, VCH, New York, 1989.
5. For representative example: (a) K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 4467; (b) J. K. Still and J. H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138.
6. For representative example: J. F. Normant, A. Commerçon and J. Villiéras, Tetrahedron Lett., 1975, 1465.
7. H. C. Brown and G. A. Morandar, J. Org. Chem., 1981, 46, 645; N. Miyaura, K. Yamada and A. Suzuki, Tetrahedron Lett., 1979, 20, 3437; M. Hoshi, Y. Masuda and A. Arase, Bull. Chem. Soc. Jpn., 1983, 56, 2855; 1985, 58, 1683.
8. (a) E. Negishi, G. Lew and T. Yoshida, J. Chem. Soc., Chem. Commun., 1973, 874; (b) H. C. Brown, N. G. Bhat and Basavaiah, Synthesis, 1986, 674; (c) A. Suzuki, N. Miyaura, S. Abiko, M. Itoh, H. C. Brown, J. A. Sinclair and M. M. Midland, J. Am. Chem. Soc., 1973, 95, 3080.
9. (a) Y. Masuda, M. Hoshi and A. Arase, J. Chem. Soc., Chem. Commun., 1991, 748; (b) 1989, 266.
10. Recent reviews: A. Pelter, K. Smith and H. C. Brown, Borane Reagents, Academic Press, London, 1988; D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995; M. Vaultier and B. Carboni, Comprehensive Organometallic Chemistry II, ed. A. Mckillop, Pergamon, Oxford, 1995, vol. 11, p. 191.
11. H. C. Brown, in Organic Synthesis via Boranes, Wiley, New York, 1975.
12. J. F. Normant, Synthesis, 1972, 63.
13. Alk-1-ynes are known to couple in the presence of copper(II) acetate: G. Eglinton and A. R. Galbrath, Chem. Ind., 1956, 737.
14. G. W. Kabalka, T. M. Shoup and N. G. Goudgaon, Tetrahedron Lett., 1989, 1483.
15. For more recent report: G. W. Kabalka, S. Yu and N.-S. Li, Tetrahedron Lett., 1997, 38, 5455; 7681.
16. B. P. Andreini, A. Carpita, R. Rossi and B. Scamuzzi, Tetrahedron, 1989, 45, 5621.