title: Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions.
abstract: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful.
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China).
authors.forename: Jun
authors.initials: J
authors.lastname: Xuan
authors.forename: Xu-Dong
authors.initials: XD
authors.lastname: Xia
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Zeng
authors.forename: Zhu-Jia
authors.initials: ZJ
authors.lastname: Feng
authors.forename: Jia-Rong
authors.initials: JR
authors.lastname: Chen
authors.forename: Liang-Qiu
authors.initials: LQ
authors.lastname: Lu
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Xiao
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001389:Azirines / Q000737:chemistry; D002384:Catalysis; D004396:Coloring Agents / Q000737:chemistry; D061565:Cycloaddition Reaction; D004735:Energy Transfer; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D008027:Light; D008670:Metals / Q000737:chemistry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001389:Azirines; D004396:Coloring Agents; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D008670:Metals; D011758:Pyrroles
keywords: cycloaddition; dyes; heterocycles; photochemistry; synthetic methods