Lewis acid-catalyzed trans-hydrosilylation of alkynes

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7654-7655

  Asao, Naoki ^a   Sudo, Tomoko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000852031     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961508g     Document Type: Article

References (30)

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3. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic: London, 1988.
4. (b) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer: Berlin, 1983.
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8. Transition metal complexes derived from Pt, Ir, Pd, Rh, Ru, Ni, Co, Fe, Re, and Mn metals have been used for hydrosilylation; see ref 1a.
9. 3-catalyzed hydrosilylation of alkynes had been reported by Voronkov's group, detailed information on regio- and stereoselectivities and generality of the reaction are not available; see: (a) Voronkov, M. G.; Adamovich, S. N.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1982, 52, 2058. (b) Voronkov, M. G.; Adamovich, S. N.; Sherstyannikova, L. V.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 706. (c) W. Ger. Pat. 2, 804, 204 (1979); Chem. Abstr. 1979, 91, 193413x. (d) Br. Pat. 684, 597 (1953); Chem. Abstr. 1954, 2761d. (e) U.S. Pat. 2, 555, 589 (1971); Chem. Abstr. 1951, 8814.
10. 3-catalyzed hydrosilylation of alkynes had been reported by Voronkov's group, detailed information on regio- and stereoselectivities and generality of the reaction are not available; see: (a) Voronkov, M. G.; Adamovich, S. N.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1982, 52, 2058. (b) Voronkov, M. G.; Adamovich, S. N.; Sherstyannikova, L. V.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 706. (c) W. Ger. Pat. 2, 804, 204 (1979); Chem. Abstr. 1979, 91, 193413x. (d) Br. Pat. 684, 597 (1953); Chem. Abstr. 1954, 2761d. (e) U.S. Pat. 2, 555, 589 (1971); Chem. Abstr. 1951, 8814.
11. 3-catalyzed hydrosilylation of alkynes had been reported by Voronkov's group, detailed information on regio- and stereoselectivities and generality of the reaction are not available; see: (a) Voronkov, M. G.; Adamovich, S. N.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1982, 52, 2058. (b) Voronkov, M. G.; Adamovich, S. N.; Sherstyannikova, L. V.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 706. (c) W. Ger. Pat. 2, 804, 204 (1979); Chem. Abstr. 1979, 91, 193413x. (d) Br. Pat. 684, 597 (1953); Chem. Abstr. 1954, 2761d. (e) U.S. Pat. 2, 555, 589 (1971); Chem. Abstr. 1951, 8814.
12. 3-catalyzed hydrosilylation of alkynes had been reported by Voronkov's group, detailed information on regio- and stereoselectivities and generality of the reaction are not available; see: (a) Voronkov, M. G.; Adamovich, S. N.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1982, 52, 2058. (b) Voronkov, M. G.; Adamovich, S. N.; Sherstyannikova, L. V.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 706. (c) W. Ger. Pat. 2, 804, 204 (1979); Chem. Abstr. 1979, 91, 193413x. (d) Br. Pat. 684, 597 (1953); Chem. Abstr. 1954, 2761d. (e) U.S. Pat. 2, 555, 589 (1971); Chem. Abstr. 1951, 8814.
13. 3-catalyzed hydrosilylation of alkynes had been reported by Voronkov's group, detailed information on regio- and stereoselectivities and generality of the reaction are not available; see: (a) Voronkov, M. G.; Adamovich, S. N.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1982, 52, 2058. (b) Voronkov, M. G.; Adamovich, S. N.; Sherstyannikova, L. V.; Pukhnarevich, V. B. J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 706. (c) W. Ger. Pat. 2, 804, 204 (1979); Chem. Abstr. 1979, 91, 193413x. (d) Br. Pat. 684, 597 (1953); Chem. Abstr. 1954, 2761d. (e) U.S. Pat. 2, 555, 589 (1971); Chem. Abstr. 1951, 8814.
14. 3-catalyzed hydrosilylation of alkenes was reported; see: (a) Oertle, K.; Wetter, H. F. Tetrahedron Lett. 1985, 26, 5511. (b) Wetter, H. F.; Oertle, K. Tetrahedron Lett. 1985, 26, 5515. (c) Yamamoto, K.; Takemae, M. Synlett 1990, 259.
15. 3-catalyzed hydrosilylation of alkenes was reported; see: (a) Oertle, K.; Wetter, H. F. Tetrahedron Lett. 1985, 26, 5511. (b) Wetter, H. F.; Oertle, K. Tetrahedron Lett. 1985, 26, 5515. (c) Yamamoto, K.; Takemae, M. Synlett 1990, 259.
16. 3-catalyzed hydrosilylation of alkenes was reported; see: (a) Oertle, K.; Wetter, H. F. Tetrahedron Lett. 1985, 26, 5511. (b) Wetter, H. F.; Oertle, K. Tetrahedron Lett. 1985, 26, 5515. (c) Yamamoto, K.; Takemae, M. Synlett 1990, 259.
17. (a) Hydroboration, see: Smith, K.; Pelter, A.; Brown, H. C. Borane Reagents; Academic Press: London, 1988. Smith, K.; Pelter, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, p 703.
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28. 3 to the acetylene takes place, in order to capture instantaneously an activated triple bond.
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30. (b) Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4784.