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Electrochemical C−H Amidation of Heteroarenes with N ‐Alkyl Sulfonamides in Aqueous Medium
Author(s) -
Zhang Yan,
Lin Zhipeng,
Ackermann Lutz
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004229
Subject(s) - chemistry , benzofuran , benzothiophene , electrochemistry , radical , electrocatalyst , catalysis , combinatorial chemistry , cyclic voltammetry , alkyl , organic chemistry , electrode , thiophene
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.