Convenient mild and selective hydrophosphination of functionalized alkenes: Access to P,O and P,S derivatives

Synthesis

Volumn , Issue 19, 2008, Pages 3121-3125

  Join, Benoit ^a   Lohier, Jean François ^a   Delacroix, Olivier ^a   Gaumont, Annie Claude ^a  

^a CNRS   (France)

Author keywords

Addition reactions; Alkenes; Boron; Phosphorus; Radical reactions

Indexed keywords

BORON COMPOUNDS; ETHERS; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS; SEMICONDUCTING INDIUM GALLIUM ARSENIDE;

ADDITION REACTIONS; ALKENES; BORON; PHOSPHORUS; RADICAL REACTIONS;

PHOSPHORUS COMPOUNDS;

ALKENE; BORANE DERIVATIVE; BORON; LIGAND; PHOSPHINE; PHOSPHORUS; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 53949091631     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067275     Document Type: Article

References (35)

1. See, for example: van Leeuwen, P. W. N. M. Homogeneous Catalysis, Understanding the Art; Kluwer Academic Publishers: Dordrecht, 2004.
2. For a recent review on hydrophosphination of alkene and alkyne derivatives, see: Delacroix, O.; Gaumont, A.-C. Curr. Org. Chem. 2005, 9, 1851.
3. For examples of hydrophosphination with alkenes, see: (a) Vallette, H.; Pican, S.; Boudou, C.; Levillain, J.; Plaquevent, J.-C.; Gaumont, A.-C. Tetrahedron Lett. 2006, 47, 5191.
4. (b) Mimeau, D.; Delacroix, O.; Join, B.; Gaumont, A.-C. C. R. Chim. 2004, 7, 845.
5. (c) Mimeau, D.; Delacroix, O.; Gaumont, A.-C. Chem. Commun. 2003, 2928 .
6. For examples with alkynes, see: (d) Join, B.; Mimeau, D.; Delacroix, O.; Gaumont, A.-C. Chem. Commun. 2006, 3249.
7. (e) Mimeau, D.; Gaumont, A.-C. J. Org. Chem. 2003, 68, 7016.
8. For example with Michael acceptors, see: (f) Join, B.; Delacroix, O.; Gaumont, A.-C. Synlett 2005, 1881.
9. (g) Bourumeau, K.; Gaumont, A.-C.; Denis, J.-M. Tetrahedron Lett. 1997, 38, 1923.
10. For example with carbonyles, see: (h) Bourumeau, K.; Gaumont, A.-C.; Denis, J.-M. J. Organomet. Chem. 1997, 529, 205.
11. For examples of C-P coupling, see: (a) Julienne, D.; Lohier, J.-F.; Delacroix, O.; Gaumont, A.-C. J. Org. Chem. 2007, 72, 2247.
12. (b) Pican, S.; Gaumont, A.-C. Chem. Commun. 2005, 2393.
13. For reviews, see: (a) Gaumont, A.-C.; Carboni, B. In Science of Synthesis, Vol. 6; Kaufmann, D. E.; Matesson, D. S., Eds.; Thieme Verlag: Stuttgart, 2005, 485-512.
14. (b) Brunel, J.-M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665.
15. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Borner, A. Synthesis 1998, 1391.
16. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
17. Transfer of the borane group from a phosphorus to an oxygen atom was already mentioned in the literature: see ref. 6.
18. See, for example: (a) Lindner, E.; Wald, J.; Eichele, K.; Fawzi, R. J. Organomet. Chem. 2000, 601, 220.
19. (b) Valls, E.; Suades, J. Organometallics 1999, 18, 5475.
20. (c) Rogers, C. W.; Wolf, M. O. Chem. Commun. 1999, 2297.
21. (a) Lindner, E.; Schmid, M.; Wegner, P.; Nachtigal, C.; Steinmann, M.; Fawzi, R. Inorg. Chim. Acta 1999, 296, 103.
22. (b) Dombek, B. D. J. Org. Chem. 1978, 43, 3408.
23. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
24. The anti-Markovnikov regioselectivity is similar to that obtained under UV irradiation or AIBN activation with free phosphines as reported by: Trofimov, B. A.; Gusarova, N. K.; Malysheva, S. F.; Ivanova, N. I.; Sukhov, B. G.; Belogorlova, N. A.; Kuimov, V. A. Synthesis 2002, 2207.
25. With a simple alkene such as oct-1-ene, the hydrophosphination could be carried out at 80°C without any decomplexation and oxidative side reactions (see ref. 3b).
26. Hirai, T.; Han, L.-B. Org. Lett. 2007, 9, 53.
27. See, for example: (a) Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059.
28. (b) Mase, N.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 1999, 40, 2797.
29. (c) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547.
30. Deprele, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745.
31. Pellon, P. Tetrahedron Lett. 1992, 33, 4451.
32. Lebel, H.; Morin, S.; Paquet, V. Org. Lett. 2003, 5, 2347.
33. (a) Trippett, S.; Corfield, J. R.; De'ath, N. J. J. Chem. Soc. C 1971, 1930.
34. (b) Harger, M. J. P. J. Chem. Soc., Perkin Trans. 1 1975, 514.
35. Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317.