Rhodium(II)- or Copper(I)-Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp2 )-H Bonds: Access to Substituted 1H-Indenes

Angewandte Chemie
Qi ZhouJianbo Wang

Abstract

A rhodium(II)- or copper(I)-catalyzed formal intramolecular carbene insertion into vinylic C(sp2 )-H bonds is reported herein. This method provides straightforward access to 1H-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.

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Citations

Jan 17, 2020·Chemistry, an Asian Journal·Debapratim DasRajarshi Samanta
Jan 21, 2020·Chemical Society Reviews·Dong ZhuShifa Zhu
Jun 25, 2021·Chemical Science·Pu ChenMichal Szostak
Aug 30, 2019·The Journal of Organic Chemistry·Meng-Yang ChangHsing-Yin Chen

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