title: Palladium-catalyzed cross-coupling of N-sulfonylaziridines with boronic acids.
abstract: A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.
authors.affiliation: Department of Chemistry, University of Washington , Box 351700, Seattle, Washington 98195-1700, United States.
authors.forename: Megan L
authors.initials: ML
authors.lastname: Duda
authors.forename: Forrest E
authors.initials: FE
authors.lastname: Michael
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D010165:Palladium / Q000737:chemistry*
chemical_list: D001388:Aziridines; D001897:Boronic Acids; D008024:Ligands; D010165:Palladium