American Chemical Society
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TMSCl-Catalyzed Electrophilic Thiocyano Oxyfunctionalization of Alkenes Using N‑Thiocyano-dibenzenesulfonimide

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journal contribution
posted on 2019-06-20, 00:00 authored by Ai-Hui Ye, Ye Zhang, Yu-Yang Xie, Hui-Yun Luo, Jia-Wei Dong, Xiao-Dong Liu, Xu-Feng Song, Tongmei Ding, Zhi-Min Chen
Numerous electrophilic thiocyano oxyfunctionalization reactions of alkenes have been achieved using N-thiocyano-dibenzenesulfonimide, which is a new electrophilic thiocyanation reagent and could be easily prepared in two steps from dibenzenesulfonimide. This approach provides efficient, simple, and modular methods for the formation of SCN-containing heterocycles such as lactones, tetrahydrofurans, dihydrofurans, and dihydrobenzofurans in moderate to excellent yields. Meanwhile, diverse oxa-quaternary centers were rapidly constructed. Additionally, this protocol is free of transition metals and features broad substrate toleraance and mild reaction conditions.