title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701 (USA) http://www.zhenggroup.org.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701 (USA) http://www.zhenggroup.org. nzheng@uark.edu.
authors.forename: Nan
authors.initials: N
authors.lastname: Zheng
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D008027:Light; D010084:Oxidation-Reduction
chemical_list: D000814:Aniline Compounds; D002244:Carbon; C023650:aniline
keywords: N-aryl cyclobutyl amines; cyclohexenes; iridium catalyst; photocatalysis; small ring systems