title: Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.
abstract: The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors: Tiezheng
authors: T
authors: Jia
authors: Ana
authors: A
authors: Bellomo
authors: Kawtar E L
authors: KE
authors: Baina
authors: Spencer D
authors: SD
authors: Dreher
authors: Patrick J
authors: PJ
authors: Walsh
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D013454:Sulfoxides; D010165:Palladium