J Org Chem. 2010 Apr 16;75(8):2756-9 doi: 10.1021/jo100344k.

Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions

Rosen BR, Ney JE, Wolfe JP.

Abstract

The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)(2) and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method.

PMID: 20297834