title: Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C-F Bonds.
abstract: We report the generation of aliphatic and benzylic acetylenes via reaction of primary, secondary, and tertiary aliphatic fluorides with various trimethylsilyl acetylides. These reactions are catalyzed by Al and B Lewis acids, most effectively by the extremely fluorophilic tris(pentafluorophenyl)alane, representing the first example of catalytic incorporation of alkynes into aliphatic C-F positions. The fluorophilicity of the catalysts gives rise to fluorine selectivity over other halogens, allowing orthogonal reactivity pathways.
authors.affiliation: Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543.
authors.forename: Amit K
authors.initials: AK
authors.lastname: Jaiswal
authors.affiliation: Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543.
authors.forename: Kelvin K K
authors.identifier: 0000-0001-6740-2176
authors.initials: KK
authors.lastname: Goh
authors.affiliation: Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543.
authors.forename: Simon
authors.identifier: 0000-0002-7864-7694
authors.initials: S
authors.lastname: Sung
authors.affiliation: Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543.
authors.forename: Rowan D
authors.identifier: 0000-0001-7437-8944
authors.initials: RD
authors.lastname: Young