Richard Y Liu1, Minwoo Bae1, Stephen L Buchwald1. 1. Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Abstract
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.
n class="Chemical">Metaln>-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.
Authors: Laura M Dornan; Qun Cao; James C A Flanagan; James J Crawford; Matthew J Cook; Mark J Muldoon Journal: Chem Commun (Camb) Date: 2013-07-11 Impact factor: 6.222