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Electrochemical C−H Amidation of Heteroarenes with N‐Alkyl Sulfonamides in Aqueous Medium
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2020-10-21 , DOI: 10.1002/chem.202004229
Yan Zhang 1, 2 , Zhipeng Lin 1 , Lutz Ackermann 1
Affiliation  

The construction of C−N bonds by free radical reactions represents a powerful synthetic approach for direct C−H amidations of arenes or heteroarenes. Developing efficient and more environmentally friendly synthetic methods for C−H amidation reactions remains highly desirable. Herein, metal‐free electrochemical oxidative dehydrogenative C−H amidations of heteroarenes with N‐alkylsulfonamides have been accomplished. The catalyst‐ and chemical‐oxidant‐free C−H amidation features an ample scope and employs electricity as the green and sole oxidant. A variety of heteroarenes, including indoles, pyrroles, benzofuran and benzothiophene, thereby underwent this C(sp2)−H nitrogenation. Cyclic voltammetry studies and control experiments provided evidence for nitrogen‐centered radicals being directly generated under metal‐free electrocatalysis.

中文翻译:

N-烷基磺酰胺在水介质中杂芳烃的电化学CH酰胺化

通过自由基反应构建C-N键代表了对芳烃或杂芳烃直接C-H酰胺化的强大合成方法。为CH酰胺化反应开发高效且对环境友好的合成方法仍然是非常可取的。在此,杂芳烃与N-烷基磺酰胺的无金属电化学氧化脱氢CHH酰胺化反应已经完成。不含催化剂和化学氧化剂的CHH酰胺化反应范围广,并使用电作为绿色和唯一的氧化剂。各种杂芳烃,包括吲哚,吡咯,苯并呋喃和苯并噻吩,都经过了这种C(sp 2)-H氮化。循环伏安法研究和控制实验为无金属电催化直接生成以氮为中心的自由基提供了证据。
更新日期:2020-10-21
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