title: Copper-Catalyzed Perfluoroalkylthiolation of Alkynes with Perfluoroalkanesulfenamides.
abstract: Copper-catalyzed direct perfluoroalkylthiolation of alkynes by using the corresponding perfluoroalkanesulfenamide reagent is reported. The selective mono- and bis-perfluoroalkylthiolation of alkynes can be conducted under very mild conditions (no base, room temperature) in very good to excellent yields. This approach, which uses a low toxicity, inexpensive copper catalyst that incorporates a commercially available ligand, is applied in the absence of any additional base. Preliminary mechanistic investigations shed some light on the nature of the unprecedented reactivity observed.
authors.affiliation: Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, Université Claude Bernard-Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622, Villeurbanne, France. anis.tlili@univ-lyon1.fr.
authors.forename: Anis
authors.initials: A
authors.lastname: Tlili
authors.affiliation: Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, Université Claude Bernard-Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622, Villeurbanne, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Alazet
authors.affiliation: Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, Université Claude Bernard-Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622, Villeurbanne, France.
authors.forename: Quentin
authors.initials: Q
authors.lastname: Glenadel
authors.affiliation: Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, Université Claude Bernard-Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622, Villeurbanne, France. thierry.billard@univ-lyon1.fr.|CERMEP - in vivo imaging, Groupement Hospitalier Est, 59 Bd Pinel, 69003, Lyon, France. thierry.billard@univ-lyon1.fr.
authors.forename: Thierry
authors.initials: T
authors.lastname: Billard
keywords: copper; cross-coupling; fluorine; trifluoromethanesulfenamide; trifluoromethylthiolation