title: Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones.
abstract: A copper-catalyzed difunctionalizing trifluoromethylation of activated alkynes with the cheap reagent sodium trifluoromethanesulfinate (NaSO2CF3 or Langlois' reagent) has been developed incorporating a tandem cyclization/dearomatization process. This strategy affords a straightforward route to synthesis of 3-(trifluoromethyl)-spiro[4.5]trienones, and presents an example of difunctionalization of alkynes for simultaneous formation of two carbon-carbon single bonds and one carbon-oxygen double bond.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-891-2582.
authors.forename: Hui-Liang
authors.initials: HL
authors.lastname: Hua
authors.forename: Yu-Tao
authors.initials: YT
authors.lastname: He
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Qiu
authors.forename: Ying-Xiu
authors.initials: YX
authors.lastname: Li
authors.forename: Bo
authors.initials: B
authors.lastname: Song
authors.forename: Pin
authors.initials: P
authors.lastname: Gao
authors.forename: Xian-Rong
authors.initials: XR
authors.lastname: Song
authors.forename: Dong-Hui
authors.initials: DH
authors.lastname: Guo
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D054879:Halogenation; D008745:Methylation; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D013141:Spiro Compounds; D003300:Copper
keywords: copper; cyclization; radical reactions; tandem reactions; trifluoromethylation