Vinylborane and vinyichalcogenide mediated syntheses of tri- and tetrasubstituted olefins from 1-alkynes

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8735-8738

  Gerard, Julien ^a   Bietlot, Emerance ^a   Hevesi, Làszlo ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORANE DERIVATIVE; METAL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032547978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01938-8     Document Type: Article

References (26)

1. 1. See for example in Comprehensive Organic Synthesis, Eds. Trost, B. M., and Fleming, I., Pergamon Press, Oxford, 1991: Kelly, S. E. in Vol. 1, p.729; Knochel, P. in Vol. 4, p.865; Krebs, A., and Swienty-Busch, J. in Vol. 6, p.949; Smith, K., and Pelter, A. in Vol. 8, p.703.
2. 1. See for example in Comprehensive Organic Synthesis, Eds. Trost, B. M., and Fleming, I., Pergamon Press, Oxford, 1991: Kelly, S. E. in Vol. 1, p.729; Knochel, P. in Vol. 4, p.865; Krebs, A., and Swienty-Busch, J. in Vol. 6, p.949; Smith, K., and Pelter, A. in Vol. 8, p.703.
3. 1. See for example in Comprehensive Organic Synthesis, Eds. Trost, B. M., and Fleming, I., Pergamon Press, Oxford, 1991: Kelly, S. E. in Vol. 1, p.729; Knochel, P. in Vol. 4, p.865; Krebs, A., and Swienty-Busch, J. in Vol. 6, p.949; Smith, K., and Pelter, A. in Vol. 8, p.703.
4. 1. See for example in Comprehensive Organic Synthesis, Eds. Trost, B. M., and Fleming, I., Pergamon Press, Oxford, 1991: Kelly, S. E. in Vol. 1, p.729; Knochel, P. in Vol. 4, p.865; Krebs, A., and Swienty-Busch, J. in Vol. 6, p.949; Smith, K., and Pelter, A. in Vol. 8, p.703.
5. 1. See for example in Comprehensive Organic Synthesis, Eds. Trost, B. M., and Fleming, I., Pergamon Press, Oxford, 1991: Kelly, S. E. in Vol. 1, p.729; Knochel, P. in Vol. 4, p.865; Krebs, A., and Swienty-Busch, J. in Vol. 6, p.949; Smith, K., and Pelter, A. in Vol. 8, p.703.
6. 2. Negishi, E.-I. and Choueiry, D. in Comprehensive Organic Functional Group Transformations, Vol. 2, p. 951, Ed. Ley, S. V., Pergamon, 1995.
7. 3. For a summary and references see Hevesi, L., in Comprehensive Organic Functional Group Transformations, Vol.2, p.899, Ed. Ley, S. V., Pergamon, 1995.
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15. 6. Petragnani, N., Tellurium in Organic Synthesis, Academic Press, London, 1994.
16. 2=Et) with PhSCl. In our case all of the compounds 2 appeared to have E stereochemistry.
17. 2, eluent pentane).
18. 9. Hoshi, M., Masuda. Y., and Arase, A., Bull. Chem. Soc. Jpn., 1990, 63, 447.
19. 10. Compounds 5 represent stereoisomeric counterparts of analogues obtained through Pd(0) catalyzed thioboration of 1-alkynes: Ishiyama, T., Nishijima, K., Miyaura, N., and Suzuki, A., J. Am. Chem. Soc., 1993, 115. 7219.
20. 11. Comasseto, J. V., in Reviews on Heteroatom Chemistry, Vol. 9 p. 61, Ed. Oae, S., MYU, Tokyo, 1993.
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22. 13. Yields are based on unrecovered 8. Premature termination of the reaction seems to be due to poisoning of the catalyst (possibly by the vinylthiolale arising from insertion of Ni(0) into the Ph-Y bond).
23. 14. Rcgioisomeric analogues of vinylsulfides 11 have been prepared using a catalytic hydroboration-coupling sequence:
24. a)Gridnev, I. D., Miyaura, N., and Suzuki, A., Organometallics, 1993, 12, 589:
25. b) Gridnev, I. D., Miyaura, N., and Suzuki, A., J. Org. Chem., 1993, 55, 5351.
26. 15. The conversion in this latter reaction was only about 50%, possibly due to the poisoning of the nickel catalyst.