Palladium-catalyzed cross-coupling of benzylzinc reagents with methylthio N-heterocycles: A new coupling reaction with unusual selectivity

Abstract

Benzylzinc reagents undergo palladium-catalyzed cross-coupling reactions with methylthio-substituted N-heterocycles in moderate to good yields. 2- (Methylthio)pyrimidines are particularly reactive substrates for this reaction. As a result, the regioselectivity of 2,4-bis(methylthio)pyrimidines is opposite to that of their 2,4-dichloropyrimidine analogues. This unusual cross-coupling reaction offers new flexibility in the regioselective synthesis of substituted pyrimidines and other heterocycles.