title: Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.
abstract: Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated. Competition experiments established the reactivity of PhNMe(3)OTf relative to PhCl, PhBr, PhI, and PhOTf.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. jonathan.reeves@boehringer-ingelheim.com
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Fandrick
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D002384:Catalysis; D008698:Mesylates / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013696:Temperature
chemical_list: D008698:Mesylates; D000644:Quaternary Ammonium Compounds; C078465:methyl triflate; D010165:Palladium