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

Angew Chem Int Ed Engl

Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701 (USA) http://www.zhenggroup.org.

Published: September 2015

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4653064PMC
http://dx.doi.org/10.1002/anie.201504076DOI Listing

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