Nickel(i)-catalyzed (de)hydrogenative coupling of amines and alkyl heteroarenes with alcohols

Abstract

A novel nickel(I) complex (di(2,2′-(1-phenyl-1H-1,2,4-triazole-3,5-diyl)dipyridine))(dibromine) nickel(I)bromide ([Ni-N₄]Br) exhibited extremely high efficiency toward the (de)hydrogenative alkylation of amines and alkyl heteroarenes by alcohols. The catalytic performance can be attributed to the functionalized nitrogen ligand, which adopts a cationic coordination mode and the facile dissociation of coordinated water. This sustainable transformation is applicable to various alcohols, featuring good functional group tolerance with high selectivity under solvent free conditions. The synthetic strategy provides a green and efficient method for the construction of functionalized amines and unsaturated N-heteroaromatic derivatives.