Rhodium-Catalyzed Transnitrilation of Aryl Boronic Acids with Dimethylmalononitrile.
An efficient transnitrilation of aryl boronic acids with dimethylmalononitrile (DMMN) is described. This rhodium-catalyzed electrophilic cyanation presents a novel approach to prepare aryl nitriles by using a carbon-bound cyanating reagent which undergoes cross-coupling with the aryl boronic acid. The reaction expands the degree of functional-group compatibility exhibited by the transnitrilation of aryl Grignard and aryllithium reagents. A variety of aryl boronic acid derivatives and dialkylmalononitriles were amenable to the transnitrilation.
Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA).
Christian A
CA
Malapit
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877-0368 (USA). jonathan.reeves@boehringer-ingelheim.com.
Jonathan T
JT
Reeves
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877-0368 (USA).
Carl A
CA
Busacca
Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA).
Amy R
AR
Howell
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877-0368 (USA).
Chris H
CH
Senanayake
boron; cross-coupling; nitriles; rhodium; synthetic methods