Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion

Abstract

An efficient Rh(III)-catalyzed straightforward strategy is developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp³) C–H functionalization. The method is mild, simple and regioselective with various ring sizes and has good functional group tolerance. The method proceeds via C8-methyl metalation, metal–carbene formation and a subsequent migratory insertion. High dilution is not necessary for this macrocyclization and the only byproduct is nitrogen. A preliminary investigation shows that the C–H metalation step is the rate-determining step.