A novel method of C-C bond formation via phenylation of terminal acetylenes by triphenylbismuth difluoride

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4051-4054

  Lermontov, Sergei A ^a   Rakov, Igor M ^a   Zefirov, Nikolai S ^a   Stang, Peter J ^b  

^a INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BIPHENYL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029940453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00730-7     Document Type: Article

References (19)

1. Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1984, 54, 2157-2158; Barton, D. H. R.; Finet, J-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622; Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1985, 55, 2514-2519.
2. Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1984, 54, 2157-2158; Barton, D. H. R.; Finet, J-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622; Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1985, 55, 2514-2519.
3. Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1984, 54, 2157-2158; Barton, D. H. R.; Finet, J-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622; Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1985, 55, 2514-2519.
4. Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1985, 55, 466-467; Barton, D. H. R.; Finet, J-P.; Pichon, C. J. Chem. Soc., Chem. Commun. 1986, 65-66.
5. Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. Zh. Obshch. Khim. (Russ.) 1985, 55, 466-467; Barton, D. H. R.; Finet, J-P.; Pichon, C. J. Chem. Soc., Chem. Commun. 1986, 65-66.
6. Barton, D. H. R.; Bhatnagar, N. Y.; Blazejewski, J-C.; Charpiot, B.; Finet, J-P.; Lester, D. J.; Motherwell, W. B.; Barros Papoula, M. T. .; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1, 1985, 2657-2665.
7. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Finet, J-P.; Motherwell, W. B.; Barros Papoula, M. T.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1, 1985, 2667-2675; Barton, D. H. R.; Finet, J-P.; Giannotti, C.; Halley, F. J. Chem. Soc., Perkin Trans. 1, 1987, 241-249.
8. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Finet, J-P.; Motherwell, W. B.; Barros Papoula, M. T.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1, 1985, 2667-2675; Barton, D. H. R.; Finet, J-P.; Giannotti, C.; Halley, F. J. Chem. Soc., Perkin Trans. 1, 1987, 241-249.
9. a. Wittig, G.; Clauß, K. Annalen, 1952, 578, 136-146; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Dokl. Akad. Nauk SSSR, (Russ.) 1975, 225, 581-582; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Sorokin, A. I.; Okhlopkova, I. E. Dokl. Akad. Nauk SSSR, (Russ.) 1978, 238, 361-363; b. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Lester, D. J.; Motherwell, W. B.; Barros Papoula, M. T. J. Chem. Soc., Chem. Commun. 1980, 827-829.
10. a. Wittig, G.; Clauß, K. Annalen, 1952, 578, 136-146; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Dokl. Akad. Nauk SSSR, (Russ.) 1975, 225, 581-582; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Sorokin, A. I.; Okhlopkova, I. E. Dokl. Akad. Nauk SSSR, (Russ.) 1978, 238, 361-363; b. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Lester, D. J.; Motherwell, W. B.; Barros Papoula, M. T. J. Chem. Soc., Chem. Commun. 1980, 827-829.
11. a. Wittig, G.; Clauß, K. Annalen, 1952, 578, 136-146; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Dokl. Akad. Nauk SSSR, (Russ.) 1975, 225, 581-582; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Sorokin, A. I.; Okhlopkova, I. E. Dokl. Akad. Nauk SSSR, (Russ.) 1978, 238, 361-363; b. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Lester, D. J.; Motherwell, W. B.; Barros Papoula, M. T. J. Chem. Soc., Chem. Commun. 1980, 827-829.
12. a. Wittig, G.; Clauß, K. Annalen, 1952, 578, 136-146; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Dokl. Akad. Nauk SSSR, (Russ.) 1975, 225, 581-582; Razuvaev, G. A.; Osanova, N. A.; Sharutin, V. V. Sorokin, A. I.; Okhlopkova, I. E. Dokl. Akad. Nauk SSSR, (Russ.) 1978, 238, 361-363; b. Barton, D. H. R.; Blazejewski, J-C.; Charpiot, B.; Lester, D. J.; Motherwell, W. B.; Barros Papoula, M. T. J. Chem. Soc., Chem. Commun. 1980, 827-829.
13. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315.
14. 8.
15. Challenger, F.; Wilkinson, J. F. J. Chem. Soc., 1922, 121, part I, 91-104.
16. Muetterties, E. L.; Mahler, W.; Packer, K. J.; Schmutzler, R. Inorg. Chem., 1964, 3, 1298-1303.
17. 12 for the comparison were synthesized independently by the known procedures. 13 was prepared from benzyl chloride and lithium derivative of 3-phenylprop-2-yne-1-ol
18. Eglinton, G.; Galbraith, A. R. J. Chem. Soc., 1959, part I, 889-896.
19. Schlubach, H. H.; Repennig, K. Annalen, 1958, 614, 37-46.