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Metal‐Free Oxidative C–H Amidation of N , N′ ‐Diarylureas with PhI(OAc) 2 : Synthesis of Benzimidazol‐2‐one Derivatives
Author(s) -
Yu Jipan,
Gao Chang,
Song Zhixuan,
Yang Haijun,
Fu Hua
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500726
Subject(s) - chemistry , intramolecular force , combinatorial chemistry , catalysis , functional group , oxidative phosphorylation , halogen , ligand (biochemistry) , benzene , oxidative addition , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor , polymer
Benzimidazol‐2‐ones have various biological functions and are usually prepared by reactions of substituted benzene‐1,2‐diamines with carbonyl‐containing compounds or intramolecular N ‐arylations using substrates with carbon‐halogen bonds. However, the starting materials of these protocols are often not readily available. Herein, a simple and practical metal‐free oxidative C–H amidation of N , N′ ‐diarylureas has been developed that takes place at room temperature. This protocol uses readily available N , N′ ‐diarylureas as the starting materials and inexpensive PhI(OAc) 2 as the oxidant without the need of a catalyst, ligand, or the exclusion of air. The present method has a wide functional group tolerance and affords a new and practical strategy for the synthesis of N‐heterocycles.