Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2-Aminofurans From N-Tosylhydrazone-Bearing Thiocarbamates |
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Authors: | Shaoyu Mai Prof. Dr. Qiuling Song |
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Affiliation: | Institute of Next Generation Matter Transformation, College of Chemical Engineering at, Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian, 361021 P.R. China |
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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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Keywords: | copper dimers heterocycles hydrazones sulfur |
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