Generation of Sulfonyl Radicals from Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: The Synthesis of 3‐Sulfonated Coumarins |
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| Authors: | Danqing Zheng Jiyao Yu Prof. Dr. Jie Wu |
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| Affiliation: | 1. Department of Chemistry, Fudan University, Shanghai, China;2. Department of Chemistry Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA-, USA;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China |
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| Abstract: | A catalyst‐free approach for the generation of sulfonyl radicals from aryldiazonium tetrafluoroborates in the presence of DABCO?(SO2)2 is realized. The combination of aryldiazonium tetrafluoroborates, DABCO?(SO2)2, and aryl propiolates affords 3‐sulfonated coumarins in good to excellent yields. This tandem reaction process involves radical addition, spirocyclization, and 1,2‐migration of esters. Additionally, the in situ diazotization of a number of anilines allows the directional synthesis of desired 3‐sulfonated coumarins in a one‐pot, two‐step process. |
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| Keywords: | diazo compounds heterocycles radicals sulfur synthetic methods |
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