Intramolecular homolytic substitution of sulfinates and sulfinamides.
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.
Coulomb
Julien
J
UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France.
Certal
Victor
V
Larraufie
Marie-Hélène
MH
Ollivier
Cyril
C
Corbet
Jean-Pierre
JP
Mignani
Gérard
G
Fensterbank
Louis
L
Lacôte
Emmanuel
E
Malacria
Max
M