Nickel-Catalyzed Oxidative C-H/N-H Isocyanide Insertion: An Efficient Synthesis of Iminoisoindolinone Derivatives

Abstract

Transition metal-catalyzed isocyanide insertion has served as a fundamental and important chemical transformation. Classical isocyanide insertion usually occurs between organohalides and nucleophiles, which normally involves tedious and non-atom-economical prefunctionalization processes. However, oxidative C-H/N-H isocyanide insertion offers an efficient and green alternative. Herein, a nickel-catayzed oxidative C-H/N-H isocyanide insertion of aminoquinoline benzamides has been developed. Different kinds of iminoisoindolinone derivatives could be synthesized in good yields by utilizing Ni(acac)2 as the catalyst. In this transformation, isocyanide serves as an efficient C1 connector, which further inserted into two simple nucleophiles (C-H/N-H), representing an effective way to construct heterocycles.

Keywords: heterocycles; iminoisoindolinone derivatives; nickel-catalyzed; oxidative C−H/N−H isocyanide insertion; oxidative cross-couplings.