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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709375
Subject(s) - carbene , intramolecular force , rhodium , chemistry , nucleophile , catalysis , medicinal chemistry , copper , stereochemistry , 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.