BENZOTRIAZOLE-MEDIATED ARYLALKYLATION AND HETEROARYLALKYLATION

An electron donor can activate a benzotriazole group through a conjugated system of type D-(CH = CH)CH,Bt. If the conjugated system is a benzene or heterocycle this enables arylalkylation and heteroarylation reactions in which Bt is replaced by alkyl or aryl groups from Grignard reagents, by hydrogen from LiA1H(4) and by other nucleophiles including electron-rich aromatic systems, alcohols, thiols, etc. Such reactions enable specific para-substitution of anilines, ortho-substitution of phenols, and elaboration of phenol ethers and heterocycles. Their scope is increased by the possibility of deprotonation of the original system at the CH2 and subsequent reaction with electrophiles before the Bt displacement.