title: Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.
abstract: The development of a gold(I)-catalyzed sulfination of aryl boronic acids is described. This transformation proceeds through an unprecedented mechanism which exploits the reactivity of gold(I)-heteroatom bonds to form sulfinate anions. Further in situ elaboration of the sulfinate intermediates leads to the corresponding sulfones and sulfonamides, two pharmacophores routinely encountered in drug discovery.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA).
authors.forename: Miles W
authors.initials: MW
authors.lastname: Johnson
authors.forename: Scott W
authors.initials: SW
authors.lastname: Bagley
authors.forename: Neal P
authors.initials: NP
authors.lastname: Mankad
authors.forename: Robert G
authors.initials: RG
authors.lastname: Bergman
authors.forename: Vincent
authors.initials: V
authors.lastname: Mascitti
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis*; D013450:Sulfones / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
chemical_list: D001897:Boronic Acids; D009942:Organometallic Compounds; D013449:Sulfonamides; D013450:Sulfones; D006046:Gold
keywords: gold; heterocycles; structure elucidation; sulfonamides; synthetic methods