ChemSusChem

Amination of Heteroaryl Chlorides: Palladium Catalysis or SNAr in Green Solvents?

K Walsh, HF Sneddon, CJ Moody

Index: Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J. ChemSusChem, 2013 , vol. 6, # 8 p. 1455 - 1460

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Citation Number: 13

Abstract

Abstract The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SN Ar reaction and N- arylation. The reaction is less satisfactory with pyridines unless an additional electron- withdrawing group is present. The results showed that the transition-metal-free SN Ar reaction not only compares favourably to palladium-catalysed coupling reactions but also ...