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Updated: Sep 15, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Photosensitized Imino-Thiocarbamation of Alkenes
Cong Huang1, Zhen-Zhen Xie1, Mei Xiang1
1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Abstract:
A metal-free, photosensitized 1,2-imino-thiocarbamation of olefins was developed using a custom-designed bifunctional reagent, diphenylmethanone O-dimethylcarbamothioyl oxime. A broad range of olefins with diverse electronic features were successfully transformed to the corresponding β-imino-thioesters, with yields ranging from moderate to high. This protocol offers several advantages, including metal-free process, 100% atom economy, simple operation, and scalability. Mechanistic investigations indicate that the triplet-triplet energy transfer and the intrinsic resonance of O-centered/S-centered carbamate radical species are crucial to the success of this strategy.
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