title: Intramolecular homolytic substitution of sulfinates and sulfinamides.
abstract: A general and efficient method for the synthesis of cyclic sulfinates and sulfinamides based on intramolecular homolytic substitution (S(H)i) at the sulfur atom by aryl or alkyl radicals is described. Both alkyl and benzofused compounds can be accessed directly from easily prepared acyclic precursors. Enantiomerically enriched sulfur-based heterocycles were formed through an S(H)i process with inversion of configuration at the sulfur atom. Cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the size of the incoming radical. 2-Pyridyl and 2-quinolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.
authors.affiliation: UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Coulomb
authors.forename: Victor
authors.initials: V
authors.lastname: Certal
authors.forename: Marie-Hélène
authors.initials: MH
authors.lastname: Larraufie
authors.forename: Cyril
authors.initials: C
authors.lastname: Ollivier
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Corbet
authors.forename: Gérard
authors.initials: G
authors.lastname: Mignani
authors.forename: Louis
authors.initials: L
authors.lastname: Fensterbank
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Lacôte
authors.forename: Max
authors.initials: M
authors.lastname: Malacria