The silicon effect on the regioselectivity of the Tsuji-Trost reaction. Experimental and theoretical approaches

Vicenç Branchadell, Marcial Moreno-Mañas, Roser Pleixats, Serge Thorimbert, Claude Commandeur, Cécile Boglio, Max Malacria
  • Journal of Organometallic Chemistry, December 2003, Elsevier
  • DOI: 10.1016/s0022-328x(03)00664-8

What is it about?

Regioselectivity of the Tsuji-Trost reaction on allyl acetates and carbonates substituted with silyl groups at the olefinic moiety has been analyzed. Silicon atom in the central carbon atom increases the stability of the intermediate π-allylpalladium cation with respect to the isomeric π-allylpalladium cation featuring the silicon in a terminal carbon atom.

Why is it important?

Silicon groups are still playing strong directing effects in organic chemistry. We have studied it in Palladium-catalyzed alkylations.

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http://dx.doi.org/10.1016/s0022-328x(03)00664-8

The following have contributed to this page: Professor Serge THORIMBERT