title: Free-Radical Carbocyanation of Olefins.
abstract: The free-radical three-component carbocyanation of electron-rich olefins was investigated with p-tosyl cyanide as cyanide source. The scope and limitations of the process were established by varying the nature of the alkene and radical precursor. Carbocyanation of chiral allylsilanes was shown to occur with high diastereocontrol, leading to syn β-silyl nitriles. The origin of the stereocontrol was rationalized by a Felkin-Anh-type transition-state model. Finally, a tin-free carbocyanation process was also devised, based on the use of a new alkylsulfonyl cyanide incorporating both carbon fragments to be added across the olefinic π system.
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Haitham
authors.initials: H
authors.lastname: Hassan
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Pirenne
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Maren
authors.initials: M
authors.lastname: Wissing
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.|Laboratoire de Chimie Appliquée et du Génie Chimique (LCAGC), Université Mouloud Mammerie de Tizi-Ouzou, 15000, Tizi-Ouzou, Algeria.
authors.forename: Chahinaz
authors.initials: C
authors.lastname: Khiar
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Ashique
authors.initials: A
authors.lastname: Hussain
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Frédéric
authors.identifier: http://orcid.org/0000-0003-2469-2067
authors.initials: F
authors.lastname: Robert
authors.affiliation: Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.
authors.forename: Yannick
authors.identifier: http://orcid.org/0000-0001-6848-6703
authors.initials: Y
authors.lastname: Landais
keywords: carbocyanation; cyanides; multicomponent reactions; radical reactions; sulfones