Rh(III)-Catalyzed Regioselective Functionalization of C–H Bonds of Naphthylcarbamates for Oxidative Annulation with Alkynes

A Rh­(III)-catalyzed highly efficient and regioselective functionalization of diverse C–H bonds of naphthylcarbamates for oxidative annulation with alkynes has been developed. The annulation with a neutral rhodium catalyst system proceeds through peri C–H bond functionalization of arylcarbamates to give benzoquinoline derivatives, while with a cationic rhodium catalyst system it proceeds through ortho C–H functionalization of arylcarbamates to furnish benzoindole derivatives.

本研究开发了一种铑(III)（Rh(III)）催化的高效且区域选择性优异的萘基氨基甲酸酯类化合物多样C-H键官能团化方法，用于与炔烃的氧化环化反应。当使用中性铑催化剂体系时，该环化反应通过芳基氨基甲酸酯的peri位C-H键官能团化进行，生成苯并喹啉类衍生物；而当使用阳离子铑催化剂体系时，反应则通过芳基氨基甲酸酯的邻位C-H键官能团化完成，得到苯并吲哚类衍生物。