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 SNAr 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 SNAr reaction not only compares favourably to palladium-catalysed coupling reactions but also operates under environmentally acceptable (“green”) conditions in terms of the base and solvent.
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