The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benz­ylation, and Cyclization Reactions

Abstract

A convenient and practical pathway to 2-cyano and 2-ester anilines is described via efficient and selective copper(II) catalyzed reductive amination via hydrosilylation process. Both 2-cyano and 2-ester anilines were successfully synthesized with good functional group tolerance and high selectivity. The application of the 2-cyano and -iodine containing anilines was developed in the synthesis of indoloindole derivatives via CuSO4 catalyzed N-benzylation and cyclization reaction in “one pot”. More interestingly, the photophysical properties investigations of these 2-cyano and 2-ester containing anilines exhibit excellent fluorescent properties which have great potential application in the development of interesting near-ultraviolet optical devices in the near future.