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TMSCl-Catalyzed Electrophilic Thiocyano Oxyfunctionalization of Alkenes Using N‑Thiocyano-dibenzenesulfonimide
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 ChenNumerous 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.
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reaction conditionselectrophilic thiocyano oxyfunctionalization reactionselectrophilic thiocyanation reagenttransition metalsAlkenesubstrate toleraancelactoneapproachmethodalkenetetrahydrofuranThiocyano-dibenzenesulfonimidedibenzenesulfonimideoxa-quaternary centersdihydrofurandihydrobenzofuranthiocyano-dibenzenesulfonimideyieldTMSCl-Catalyzed Electrophilic Thiocyano OxyfunctionalizationformationSCN-containing heterocycles