Highly active, stable, catalysts for the Heck reaction; further suggestions on the mechanism

Abstract

Tri(1-naphthyl)phosphine gives palladacycles which are very active catalysts for Heck reactions; mechanisms based on a Pd^II–Pd^IV cycle are proposed and a new, very efficient method of separating the product from the catalyst has been devised, which involves treatment with cyanide ion.

References

1. (a) W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele and M. Beller, Chem. Eur. J., 1997, 3, 1357; (b) M. Beller and T. H. Riermeier, Eur. J. Inorg. Chem., 1998, 1, 29.
2. B. L. Shaw, New J. Chem., 1998, 77.
3. J. M. Duff and B. L. Shaw, J. Chem. Soc., Dalton Trans., 1972, 2219.
4. M. T. Beck, Pure Appl. Chem., 1987, 59, 1703.
5. T. Jeffery, Tetrahedron Lett., 1994, 35, 3051 and references therein.
6. T. Kauffmann, B. Laarmann, D. Menges and G. Neiteler, Chem. Ber., 1992, 125, 163.
7. M. Ohff, A. Ohff, M. E. van der Boom and D. Milstein, J. Am. Chem. Soc., 1997, 119, 11 687.