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Updated: Jan 5, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes
Yujing Guo1, Thanh Vinh Nguyen2, Rene M Koenigs1
1Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany.
Abstract:
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.
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