Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, West Bengal, India.
Chem Asian J. 2022 Jun 1;17(11):e202200085. doi: 10.1002/asia.202200085. Epub 2022 Apr 19.
A combination of aryldiazonium salts and DABSO provides a unique opportunity for sulfonylative multicomponent cross-coupling reactions. Here, a copper-catalyzed three-component cross-coupling of aryldiazonium salts, DABSO with arylboronic acids to obtain medicinally relevant unsymmetrical diarylsulfones is disclosed. Interestingly, a catalyst-free approach for the synthesis of arylvinylsulfones from the corresponding vinyl boronic acids or vinyl halides is explored under basic condition. Tethered aryldiazonium salts provided the corresponding annulated alkylvinylsulfones via alkene difunctionalization under the same transition metal-free condition. Mechanistically, these multicomponent reactions proceed through a single electron pathway by the formation of arylsulfonyl radical as a key intermediate.
芳基重氮盐和 DABSO 的组合为磺酰化多组分交叉偶联反应提供了独特的机会。在这里，公开了一种铜催化的芳基重氮盐、DABSO 与芳基硼酸的三组分交叉偶联反应，以获得具有医学相关性的不对称二芳基砜。有趣的是，在碱性条件下，探索了无催化剂合成芳基乙烯砜的方法，该方法可由相应的乙烯基硼酸或乙烯基卤化物合成。连接的芳基重氮盐在相同的无过渡金属条件下通过烯烃双官能化反应提供了相应的稠合烷基乙烯砜。从机理上讲，这些多组分反应通过形成芳基砜基自由基作为关键中间体，通过单电子途径进行。
