Rhodium(II)‐ or Copper(I)‐Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp 2 )−H Bonds: Access to Substituted 1 H ‐Indenes | Zendy

Zhou Qi | Zendy; Li Shichao | Zendy; Zhang Yan | Zendy; Wang Jianbo | Zendy

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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.

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