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Intermolecular C−H Amidation of (Hetero)arenes to Produce Amides through Rhodium‐Catalyzed Carbonylation of Nitrene Intermediates
Author(s) -
Yuan SiWen,
Han Hui,
Li YanLin,
Wu Xueli,
Bao Xiaoguang,
Gu ZhengYang,
Xia JiBao
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903656
Subject(s) - nitrene , chemistry , rhodium , carbonylation , amide , intermolecular force , catalysis , organic synthesis , carbon monoxide , combinatorial chemistry , organic chemistry , photochemistry , molecule
Amide bond formation is one of the most important reactions in organic chemistry because of the widespread presence of amides in pharmaceuticals and biologically active compounds. Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium‐catalyzed three‐component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene‐intermediates and direct C−H functionalization. Notably, the reaction proceeds in an intermolecular fashion with N 2 as the only by‐product, and either directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh‐nitrene intermediate.