The Cleavage of a CC Bond in Cyclobutylanilines by Visible‐Light Photoredox Catalysis: Development of a [4+2] Annulation Method | Zendy

Wang Jiang | Zendy; Zheng Nan | Zendy

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The Cleavage of a CC Bond in Cyclobutylanilines by Visible‐Light Photoredox Catalysis: Development of a [4+2] Annulation Method

Author(s) -

Wang Jiang,

Zheng Nan

Publication year - 2015

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.201504076

Subject(s) - annulation , photoredox catalysis , photochemistry , photocatalysis , chemistry , bicyclic molecule , catalysis , bond cleavage , decalin , visible spectrum , intermolecular force , cleavage (geology) , amine gas treating , redox , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , molecule , optoelectronics , fracture (geology) , composite material

We report the first example of an intermolecular [4+2] annulation of cyclobutylanilines with alkynes enabled by visible‐light photocatalysis. Monocyclic and bicyclic cyclobutylanilines successfully undergo the annulation with terminal and internal alkynes to generate a wide variety of amine‐substituted cyclohexenes including new hydrindan and decalin derivatives with good to excellent diastereoselectivity. The reaction is overall redox neutral with perfect atom economy.

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