Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2-Aminofurans From N-Tosylhydrazone-Bearing Thiocarbamates

Angewandte Chemie
Shaoyu Mai, Qiuling Song

Abstract

An efficient and convenient synthesis of valuable disulfanes and benzenesulfonothioates, having a 2-aminofuran framework, has been developed by employing a copper-catalyzed transformation of readily available N-tosylhydrazone-bearing thiocarbamates. This method features an inexpensive metal catalyst, mild reaction conditions, good functional-group tolerance, short reaction times, and delivers valuable and complex products. A copper carbene generated from an N-tosylhydrazone-bearing thiocarbamate is proposed as the key intermediate for the transformation and it triggers the subsequent cascade. Remarkably, the Ts anion released from N-tosylhydrazone further serves as a nucleophile, thus rendering the formation of benzenesulfonothioates under controlled conditions.

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Citations

Sep 7, 2017·Chemical Communications : Chem Comm·Jae Bin LeeSung You Hong
Aug 3, 2018·Chemical Communications : Chem Comm·Shaoyu MaiQiuling Song
Dec 15, 2019·Nature Communications·Shaoyu MaiQiuling Song
Apr 15, 2021·Accounts of Chemical Research·Kai Yang, Qiuling Song
May 20, 2020·Journal of the American Chemical Society·Zijun Wu, Derek A Pratt

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