title: Copper-Catalyzed Cascade Transformation of Homopropargyl Azides into Trifluoromethylated Nitriles via C-C Cleavage.
abstract: A cascade reaction of homopropargyl azides in the presence of a Cu catalyst was achieved, affording 3-(trifluoromethyl)but-3-enenitriles with good yields and excellent regioselectivity. This reaction appears to be the first direct conversion of homopropargyl azides into trifluoromethylated nitriles. Mechanistic studies indicate that the transformation proceeds by addition of a CF3radical to the alkyne, C-C cleavage by 1,4-aryl radical migration, and nitrile formation. This protocol provides a novel strategy for transforming azides into nitriles via C-C cleavage derived from radical migration.
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry & Molecular Engineering, East China University of Science & Technology , Meilong Road 130, Shanghai 200237, China.
authors.forename: Shuang
authors.initials: S
authors.lastname: Chen
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry & Molecular Engineering, East China University of Science & Technology , Meilong Road 130, Shanghai 200237, China.
authors.forename: Deng-Yuan
authors.initials: DY
authors.lastname: Li
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry & Molecular Engineering, East China University of Science & Technology , Meilong Road 130, Shanghai 200237, China.
authors.forename: Liang-Liang
authors.initials: LL
authors.lastname: Jiang
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry & Molecular Engineering, East China University of Science & Technology , Meilong Road 130, Shanghai 200237, China.
authors.forename: Kai
authors.initials: K
authors.lastname: Liu
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry & Molecular Engineering, East China University of Science & Technology , Meilong Road 130, Shanghai 200237, China.
authors.forename: Pei-Nian
authors.identifier: 0000-0003-2014-2244
authors.initials: PN
authors.lastname: Liu