Brandon R Rosen1, Joshua E Ney, John P Wolfe. 1. Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
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.
The development of conditions that allow use of inexpensive aryl chlorides as electrophiles inn class="Chemical">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.
Authors: Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson Journal: Org Lett Date: 2011-11-09 Impact factor: 6.005