Electrochemical C−H Amidation of Heteroarenes with N‐Alkyl Sulfonamides in Aqueous Medium. Issue 1 (26th November 2020)

• Record Type: Journal Article
• Authors: Zhang, Yan; Lin, Zhipeng; Ackermann, Lutz
• Is Part Of: Chemistry. Volume 27:Issue 1(2021)
• Page Start: 242
• Page End: 246
• Publication Date: 2020-11-26
• Subjects: amidation -- electrochemistry -- heterocycles -- radicals -- sulfonamides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004229
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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(sp 2 )−H nitrogenation. Cyclic voltammetry studies and control experiments provided evidence for nitrogen‐centered radicals being directly generated under metal‐free electrocatalysis. Abstract : Heterocycles : Metal‐free electrochemical dehydrogenative C−H amidation of heteroarenes with N ‐alkylsulfonamides have been accomplished. The catalyst‐ and chemical oxidant‐free C−H amidation featured ample substrate scope and employed electricity as the sole oxidant (see scheme).