Allylic phosphinates via palladium-catalyzed allylation of H-phosphinic acids with allylic alcohols

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1123-1126

  Coudray, Laětitia ^a   Bravo Altamirano, Karla ^a   Montchamp, Jean Luc ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; PALLADIUM; PHOSPHINIC ACID DERIVATIVE; PROPANOL;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; PALLADIUM; PHOSPHINIC ACIDS; PROPANOLS;

EID: 45549107725     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8000415     Document Type: Article

References (38)

1. (a) Montchamp, J.-L. Specialty Chem. Mag. 2006, 26, 44. (b) Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
2. Abrunhosa-Thomas, I.; Sellers, C. E.; Montchamp, J.-L. J. Org. Chem. 2007, 72, 2851, and references cited therein.
3. (a) Xu, Y.; Zhang, J. Synthesis 1984, 778.
4. (b) Xu, Y.; Li, Z.; Xia, J.; Guo, H.; Huang, Y. Synthesis 1983, 377.
5. (c) Xu, Y.; Li, Z. Synthesis 1986, 240.
6. (d) Xu, Y.; Zhang, J. J. Chem. Soc. Chem. Commun. 1986, 1606.
7. (e) Xu, Y.; Wej, H.; Zhang, J.; Huang, G. Tetrahedron Lett. 1989, 30, 949.
8. (f) Huang, C.; Tang, X.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2006, 71, 5020.
9. (g) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636.
10. (h) Lei, H.; Stoakes, M. S.; Schwabacher, A. W. Synthesis 1992, 1255.
11. (a) Hirai, T.; Han, L.-B. Org. Lett. 2007, 9, 53.
12. (b) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233.
13. (c) Zeiss, H.-J. Tetrahedron Lett. 1992, 38, 8263.
14. (d) Dingwall, J. G.; Tuck, B. J. Chem. Soc., Perkin Trans. I 1986, 2081.
15. (e) Pudovik, A. N.; Konovalova, I. V.; Guryleva, A. A. J. Gen. Chem. USSR 1963, 33, 2850.
16. (f) Finke, M.; Kleiner, H.-J. Liebigs Ann. Chem. 1974, 741.
17. (a) Nune, S. K.; Tanaka, M. Chem. Commun. 2007, 2858.
18. (b) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.
19. (c) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080.
20. (d) Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2007, 272.
21. (e) Stockland, R. A. Jr. Taylor, R. I.; Thompson, L. E.; Patel, P. B. Org. Lett. 2005, 7, 851.
22. Deprèle, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745.
23. Bravo-Altamirano, K.; Montchamp, J.-L. Org. Lett. 2006, 8, 4169.
24. Bravo-Altamirano, K.; Montchamp, J.-L. Tetrahedron Lett 2007, 48, 5755.
25. See Supporting Information for details. The starting H-phosphinic acids are available through methods we have developed, (a) Montchamp, J.-L.; Dumond, Y. R. J. Am. Chem. Soc. 2001, 123, 510.
26. (b) Deprèle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386.
27. (c) Deprèle, S.; Montchamp, J.-L. Org. Lett. 2004, 6, 3805. (d) See also refs 1, 6, 7.
28. 2, see ref 7 and Bravo-Altamirano, K.; Abrunhosa-Thomas, I.; Montchamp, J.-L. J. Org. Chem. 2008, 73, 2292.
29. a AcOH 4.76.
30. Trost, B. M. Chem. Rev. 1996, 96, 395.
31. Unpublished results. Bravo-Altamirano, K. Ph.D. dissertation, Texas Christian University, May 2007.
32. (a) Reznik, V. S.; Levin, Y. A.; Akamsin, V. D.; Galyametdinova, I. V.; Pyrkin, R. I. Russ. Chem. Bull. 2000, 49, 495.
33. (b) Levin, Y. A.; Pyrkin, R. I.; Galyametdinova, I. Patent, U.S.S.R. 1974, SU 414264.
34. (c) Manthey, M. K.; Huang, D. T. C.; Bubb, W. A.; Christopherson, R. I. J. Med. Chem. 1998, 41, 4550.
35. Maier, L. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 66, 67.
36. (a) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2219.
37. (b) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowsky, C. Org. Lett. 2000, 2, 1517.
38. Loewus, D. I. J. Am. Chem. Soc. 1981, 103, 2292.