J.-M. Denis et al. / Tetrahedron Letters 43 (2002) 5569–5571
5571
In summary, these preliminary results demonstrate well
house, M. B. J. Chem. Soc., Dalton Trans. 2001, 1768–
1772.
the potential of the HSiR /cat-B(C F) system in silyla-
3
6
3
tion reactions and in the reduction of esters of phos-
phorus to free phosphines. The efficiency and the
simplicity of the protocol for the silylation of P-esters
make this method a useful alternative to the previously
described approaches. On the other hand, the practical
and simple reduction of phosphonates and phosphi-
nates to free phosphines is also of synthetic value. In
some instances, no work-up is necessary. This process
remains, however, mainly reserved to the structures
bearing no other reducible group in proximity of the
target P-OR function. The proposed mechanism is in
good agreement with the experimental data.
7. Bradley, D. C.; Hursthouse, M. B.; Motevalli, M.; Zheng,
D. H. J. Chem. Soc., Chem. Commun. 1991, 7–8.
8. Bradley, D. C.; Harding, I. S.; Keefe, A. D.; Motevalli,
M.; Zheng, D. H. J. Chem. Soc., Dalton Trans. 1996,
3931–3936.
9. For a recent review, see Carboni, B.; Monnier, L. Tetra-
hedron 1999, 55, 1197–1248.
10. Fritzsche, H.; Hasserodt, F.; Korte, F. Chem. Ber. 1965,
98, 1681.
11. See for example Soulier, E.; Yaouanc, J.-J.; Laurent, P.;
des Abbayes, H.; Cl e´ ment, J.-C. Eur. J. Org. Chem. 2000,
3497–3503.
1
2. (a) Gaumont, A.; Denis, J.-M. Chem. Rev. 1994, 94,
413–1439; (b) Keglevich, G.; Gaumont, A.-C.; Denis,
J.-M. Heteroat. Chem. 2001, 12, 161–167.
13. Review: Wozniak, L.; Chojnowski, J. Tetrahedron 1989,
5, 2465–2524.
1
References
4
1
. Reviews: (a) Piers, W. E.; Chivers, T. Chem. Soc. Rev.
14. (a) Cabioch, J.-L.; Pellerin, B.; Denis, J.-M. Phosphorus
Sulfur Silicon 1989, 44, 27–32; (b) Guillemin, J.-C.;
Janati, T.; Guenot, P.; Savignac, P.; Denis, J.-M. Angew.
Chem., Int. Ed. Engl. 1991, 30, 196–198.
1
997, 26, 345–354; (b) Ishihara, K.; Yamamoto, H. Eur.
J. Chem. 1999, 527–538.
2
3
4
5
6
. Parks, D. J.; Blackwell, J. B.; Piers, W. E. J. Org. Chem.
2
000, 65, 3090–3098 and references cited therein.
15. Bourumeau, K.; Gaumont, A.-C.; Denis, J.-M. J.
. Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E.
Organomet. Chem. 1997, 529, 205–213.
J. Org. Chem. 1999, 64, 4887–4892.
16. Benie, A. Ph. D. Thesis, University of Rennes, 1999.
17. Gaumont, A.-C.; Morise, X.; Denis, J.-M. J. Org. Chem.
1992, 57, 4292–4295.
. Gevorgyan, V.; Rubin, M.; Benson, S.; Lui, J.-X.;
Yamamoto, Y. J. Org. Chem. 2000, 65, 6179–6186.
. Gevorgyan, V.; Rubin, M.; Liu, J.-X.; Yamamoto, Y. J.
Org. Chem. 2001, 66, 1672–1675.
18. An analogous process was proposed for a CꢀOR bond
cleavage catalyzed by InCl ; Onishi, M. Y.; Ueba, M.;
3
. Beckett, M. A.; Brassington, D. S.; Light, M. E.; Hurst-
Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741–7744.