title: Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols.
abstract: A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.
authors.affiliation: State key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China).
authors.forename: Pin
authors.initials: P
authors.lastname: Gao
authors.forename: Yong-Wen
authors.initials: YW
authors.lastname: Shen
authors.forename: Ran
authors.initials: R
authors.lastname: Fang
authors.forename: Xin-Hua
authors.initials: XH
authors.lastname: Hao
authors.forename: Zi-Hang
authors.initials: ZH
authors.lastname: Qiu
authors.forename: Fan
authors.initials: F
authors.lastname: Yang
authors.forename: Xiao-Biao
authors.initials: XB
authors.lastname: Yan
authors.forename: Qiang
authors.initials: Q
authors.lastname: Wang
authors.forename: Xiang-Jun
authors.initials: XJ
authors.lastname: Gong
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D008745:Methylation
chemical_list: D000438:Alcohols; D005617:Chlorofluorocarbons, Methane; D003300:Copper; C009554:fluoroform
keywords: Togni’s reagent; aryl migration; copper; radical reactions; trifluoromethylation