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Copper-catalyzed synthesis of sulfonamides from nitroarenes via the insertion of sulfur dioxide.
Chemical Communications ( IF 4.3 ) Pub Date : 2020-02-26 , DOI: 10.1039/d0cc00721h Xuefeng Wang 1 , Min Yang 2 , Yunyan Kuang 1 , Jin-Biao Liu 3 , Xiaona Fan 2 , Jie Wu 4
Chemical Communications ( IF 4.3 ) Pub Date : 2020-02-26 , DOI: 10.1039/d0cc00721h Xuefeng Wang 1 , Min Yang 2 , Yunyan Kuang 1 , Jin-Biao Liu 3 , Xiaona Fan 2 , Jie Wu 4
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Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).
中文翻译：
铜催化通过插入二氧化硫从硝基芳烃合成磺酰胺。
硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。
更新日期：2020-03-20
中文翻译：
铜催化通过插入二氧化硫从硝基芳烃合成磺酰胺。
硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。
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