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Direct intramolecular C(sp3)–H bond sulfonamidation to synthesize benzosultam derivatives under metal-free conditions
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2021-10-22 , DOI: 10.1039/d1qo01235e
He Zhang 1 , Meng-Chan Sun 1 , Li-Ming Yin 1 , Donghui Wei 1 , Mao-Ping Song 1 , Dandan Yang 1 , Jun-Long Niu 1
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Direct C(sp3)–H bond amination has become a hot topic due to its high efficiency in converting the C(sp3)–H bond to the C–N bond. Herein, we report an efficient intramolecular C(sp3)–H bond sulfonamidation under metal-free conditions, which provides a straightforward method for the synthesis of 5-membered cyclic sulfonamides (benzosultams). This protocol avoids the use of metal catalysts, oxidants, and any additives. Mechanistic experiments and DFT calculations revealed that the reaction proceeds through a proton transfer coupled with the SN2 (PTSN2) process, which is different from other pathways.

中文翻译:

在无金属条件下直接分子内 C(sp3)-H 键磺酰胺化合成苯磺胺衍生物

直接的 C(sp 3 )-H 键胺化因其将 C(sp 3 )-H 键转化为 C-N 键的效率高而成为热门话题。在此,我们报告了一种在无金属条件下有效的分子内 C(sp 3 )-H 键磺酰胺化,这为合成 5 元环磺酰胺(苯并磺胺)提供了一种直接的方法。该协议避免使用金属催化剂、氧化剂和任何添加剂。机理实验和 DFT 计算表明,该反应通过质子转移和 S N 2 (PTS N 2) 过程进行,这与其他途径不同。
更新日期:2021-11-01
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