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Rhodium(II)‐ or Copper(I)‐Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp 2 )−H Bonds: Access to Substituted 1 H ‐Indenes
Author(s) -
Zhou Qi,
Li Shichao,
Zhang Yan,
Wang Jianbo
Publication year - 2017
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.201709375
Subject(s) - carbene , intramolecular force , rhodium , chemistry , nucleophile , medicinal chemistry , catalysis , stereochemistry , insertion reaction , organic chemistry
A rhodium(II)‐ or copper(I)‐catalyzed formal intramolecular carbene insertion into vinylic C(sp 2 )−H bonds is reported herein. This method provides straightforward access to 1 H ‐indenes with high efficiency and excellent functional‐group compatibility. Mechanistically, the reaction is proposed to involve the following sequence: metal carbene formation, intramolecular nucleophilic addition of the double bond to the electron‐deficient carbene carbon atom, dearomatization, and finally a 1,5‐H shift.