Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.
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.
Reeves
Jonathan T
JT
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
Fandrick
Daniel R
DR
Tan
Zhulin
Z
Song
Jinhua J
JJ
Lee
Heewon
H
Yee
Nathan K
NK
Senanayake
Chris H
CH
D002384:Catalysis; D008698:Mesylates / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013696:Temperature
D008698:Mesylates; D000644:Quaternary Ammonium Compounds; C078465:methyl triflate; D010165:Palladium