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