Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes

作者：Yujing Guo, Thành Vinh Nguyễn, René M. Koenigs · 发表于：Organic Letters · 年份：2019 · DOI：10.1021/acs.orglett.9b03453 · 被引用次数：112 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Catalytic Alkyne Reactions

Cyclopropanation reactions of carbenes with arenes provide a straightforward pathway to norcaradienes or cycloheptatrienes. This reaction normally requires harsh reaction conditions or transition-metal catalysts. In this report, we describe the metal-free visible-light photolysis of aryl diazoacetates in aromatic solvents, which provides access to the norcaradiene ring system in a highly regio- and stereoselective manner. The mild reaction conditions of this approach also allow chemoselective cyclopropanation of substituted arenes without competing C-H functionalization reactions.