title: Gold-catalyzed direct arylation.
abstract: Biaryls (two directly connected aromatic rings, Ar(1)-Ar(2)) are common motifs in pharmaceuticals, agrochemicals, and organic materials. Current methods for establishing the Ar(1)-Ar(2) bond are dominated by the cross-coupling of aryl halides (Ar(1)-X) with aryl metallics (Ar(2)-M). We report that, in the presence of 1 to 2 mole percent of a gold catalyst and a mild oxidant, a wide range of arenes (Ar(1)-H) undergo site-selective arylation by arylsilanes (Ar(2)-SiMe(3)) to generate biaryls (Ar(1)-Ar(2)), with little or no homocoupling (Ar(1)-Ar(1)/Ar(2)-Ar(2)). Catalysis proceeds at room temperature and tolerates a broad range of functional groups, including those incompatible with cross-coupling. These features expedite biaryl preparation, as demonstrated by synthesis of the nonsteroidal anti-inflammatory diflunisal.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK.
authors.forename: Liam T
authors.initials: LT
authors.lastname: Ball
authors.forename: Guy C
authors.initials: GC
authors.lastname: Lloyd-Jones
authors.forename: Christopher A
authors.initials: CA
authors.lastname: Russell
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D006841:Hydrocarbons, Aromatic; D016877:Oxidants; D004364:Pharmaceutical Preparations; D012821:Silanes; D006046:Gold