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The Cleavage of a CC 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.