Radical phosphination of organic halides and alkyl imidazole-1- carbothioates

Journal of the American Chemical Society

Volumn 128, Issue 13, 2006, Pages 4240-4241

  Sato, Akinori ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; IMIDAZOLE DERIVATIVE; ORGANOHALOGEN DERIVATIVE;

ARTICLE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE;

EID: 33645469411     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058783h     Document Type: Article

References (26)

1. Use of phosphorus-centered radicals in organic synthesis was summarized: Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858-865.
2. Addition reactions of phosphinyl radicals to carbon-carbon multiple bonds are the general radical-based approach to organophosphines: Stacey, F. W.; Harris, J. F., Jr. Org. React. 1963, 13, 150-376. For recent advances, see ref 1.
3. Our radical-based approach to organophosphines: Sato, A.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 1694-1696.
4. The synthesis of phosphonic acid by the reaction of white phosphorus with carbon-centered radicals was reported: (a) Barton, D. H. R.; Zhu, J. J. Am. Chem. Soc. 1993, 115, 2071-2072.
5. (b) Barton, D. H. R.; Vonder Embse, R. A. Tetrahedron 1998, 54, 12475-12496.
6. (a) Elsner, G. Methoden der Organischen Chemie (Houben-Weyl): Georg Thieme Verlag: Stuttgart, 1982; Vol. E1.
7. (b) Kawashima, T. In the Fourth Series of Experimental Chemistry: Akiba, K., Ed.; Maruzen: Tokyo. 1992; Vol. 24, Chapter 6.1.
8. We have developed phosphination reactions directed toward the synthesis of functionalized organophosphines: (a) Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4873-4875.
9. (b) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 2368-2370. Also see ref 3.
10. Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3641-3642. Tributyltin hydride did not serve well in the phosphination reaction. The tin hydride reacted rapidly only with chlorodiphenylphosphine to consume the tin hydride.
11. Mild reduction of phosphine sulfide to trivalent phosphine is known: Romeo, R.; Wozniak, L. A.; Chatgilialoglu, C. Tetrahedron Lett. 2000, 41, 9899-9902.
12. See Supporting Information for the procedure for the purification of products 3. The purification necessitated sequential silica gel column purification and size exclusion chromatography.
13. Separately, we confirmed that the reduction of chlorodiphenylphosphine with TTMSS took place in the presence of V-40. In the absence of V-40, the reduction did not proceed.
14. Okazaki, R.; Hirabayashi, Y.; Tamura, K.; Inamoto, N. J. Chem. Soc., Perkin Trans. 1 1976, 1034-1036.
15. H2 process was reported: Barrett, A. G. M.; Melcher, L. M. J. Am. Chem. Soc. 1991, 113, 8177-8178.
16. Methods to replace halide moieties with heteroatoms via radical processes and their analogues: (a) Ollivier, C.; Renaud, P. In Radicals in Organic Synthesis: Renaud, P., Sibi, M. P., Eds.: Wiley-VCH: Weinheim, 2001; Vol. 2, Chapter 2.1.
17. (b) Braslau, R.; Anderson, M. O. in Radicals in Organic Synthesis; Renaud, P.. Sibi, M. P., Eds.: Wiley-VCH: Weinheim, 2001; Vol. 2. Chapter 2.3.
18. (c) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: Chichester, 1995; Chapter 11.
19. (d) Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980-8982.
20. (e) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717-4727.
21. (f) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1993, 115, 5521-5522.
22. (g) Barton, D. H. R.; Bridon, D.; Zard, S. Z. Tetrahedron Lett. 1984, 25, 5777-5780.
23. (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rer. 2004, 248, 2337-2364.
24. (b) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397-7403.
25. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
26. (b) Rasmussen, J. R.; Slinger, C. J.; Kordish, R. J.; Newman-Evans, D. D. J. Org. Chem. 1981, 46, 4843-4846.