Chemistry of pentavalent organobismuth reagents. Regioselective α- arylation of α,β-unsaturated carbonyls and related systems

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6915-6917

  Arnauld, Thomas ^a   Barton, Derek H R ^a   Normant, Jean François ^b   Doris, Eric ^c  

^a TEXAS A AND M UNIVERSITY   (United States)

^b SORBONNE UNIVERSITÉ   (France)

^c INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH; CARBONYL DERIVATIVE; REAGENT;

CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; REACTION ANALYSIS;

EID: 0032885850     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9905928     Document Type: Note

References (22)

1. For reviews on bismuth chemistry see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982, 82, 15-57. Finet, J. P. Chem. Rev. 1989, 89, 1487-1501.
2. For reviews on bismuth chemistry see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982, 82, 15-57. Finet, J. P. Chem. Rev. 1989, 89, 1487-1501.
3. Arnauld, T.; Barton, D. H. R.; Doris, E. Tetrahedron 1997, 53, 4137-4144 and references cited. Barton, D. H. R.; Finet, J. P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887-890.
4. Arnauld, T.; Barton, D. H. R.; Doris, E. Tetrahedron 1997, 53, 4137-4144 and references cited. Barton, D. H. R.; Finet, J. P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887-890.
5. Barton, D. H. R; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. Barton, D. H. R.; Finet, J. P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622,
6. Barton, D. H. R; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. Barton, D. H. R.; Finet, J. P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622,
7. Barton, D. H. R.; Barros Papoula, M. T.; Guilhem, J.; Motherwell, W. B.; Pascard, C.; Tran Huu Dau, E. J. Chem. Soc., Chem. Commun. 1982, 732-734.
8. Fedorov, A.; Combes, S.; Finet, J. P. Tetrahedron 1999, 55, 1341-1352.
9. Suzuki, H.; Matano, Y. In The Chemistry of Arsenic Antimony and Bismuth; Norman, N. C., Ed.; Blackie: London, 1998; Chapter 6.
10. Herrmann, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2433-2436.
11. Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. 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 1986, 2657-2665.
12. Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. 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 1986, 2657-2665.
13. The rearrangement proceeds by ligand coupling between the ipso carbon of the aryl group and the dienolate α-carbon atom; see ref 5.
14. Barton, D. H. R.; Finet, J. P.; Giannotti, C.; Halley, F. J. Chem. Soc., Perkin Trans. 1 1987, 241-249. See also: Combes, S.; Finet, J. P. Tetrahedron 1999, 55, 3377-3386.
15. Barton, D. H. R.; Finet, J. P.; Giannotti, C.; Halley, F. J. Chem. Soc., Perkin Trans. 1 1987, 241-249. See also: Combes, S.; Finet, J. P. Tetrahedron 1999, 55, 3377-3386.
16. Beresis, R. T.; Masse, C. E.; Panek, J. S. J. Org. Chem. 1995, 60, 7714-7715.
17. 3Bi by methanesulfonic acid has recently been reported; see: Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285-286.
18. 3Bi by methanesulfonic acid has recently been reported; see: Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285-286.
19. Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132-157.
20. Phan, T. H.; Dahn, H. Helv. Chim. Acta 1976, 59, 335-348.
21. Collin, J.; Bied, C.; Kagan, H. B. Tetrahedron Lett. 1991, 32, 629-630.
22. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434-5447.