Intramolecular Metal‐Free Oxidative Aryl–Aryl Coupling: An Unusual Hypervalent‐Iodine‐Mediated Rearrangement of 2‐Substituted  N ‐Phenylbenzamides | Zendy

Shang Siyun | Zendy; ZhangNegrerie Daisy | Zendy; Du Yunfei | Zendy; Zhao Kang | Zendy

Premium

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 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.201402925

Subject(s) - hypervalent molecule , aryl , intramolecular force , chemistry , iodine , bond cleavage , medicinal chemistry , oxidative phosphorylation , oxidative addition , metal , oxidative coupling of methane , stereochemistry , 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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research