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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.

ABSTRACT: 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.

SUBMITTER: Wang J

PROVIDER: S-EPMC4653064 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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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.

Wang Jiang J Zheng Nan N

Angewandte Chemie (International ed. in English) 20150724 39

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. ...[more]

PMID: 26228259

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