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Intramolecular Metal‐Free Oxidative Aryl–Aryl Coupling: An Unusual Hypervalent‐Iodine‐Mediated Rearrangement of 2‐Substituted N ‐Phenylbenzamides
Author(s) -
Shang Siyun,
ZhangNegrerie Daisy,
Du Yunfei,
Zhao Kang
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402925
Subject(s) - hypervalent molecule , aryl , chemistry , intramolecular force , bond cleavage , iodine , oxidative addition , medicinal chemistry , oxidative phosphorylation , stereochemistry , oxidative coupling of methane , metal , organic chemistry , catalysis , alkyl , biochemistry
Hypervalent‐iodine‐mediated oxidative coupling of the two aryl groups in either 2‐acylamino‐ N ‐phenyl‐benzamides or 2‐hydroxy‐ N ‐phenylbenzamides, with concomitant insertion of the ortho ‐substituted N or O atom into the tether, has been described for the first time. This unusual metal‐free rearrangement reaction involves an oxidative C(sp 2 )C(sp 2 ) aryl–aryl bond formation, cleavage of a C(sp 2 )C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.