Article

Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.

Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA.
Organic Letters (impact factor: 5.86). 10/2010; 12(19):4388-91. DOI:10.1021/ol1018739 pp.4388-91
Source: PubMed

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.

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Keywords

ambient temperature
 
aryl Grignard reagents
 
Aryltrimethylammonium triflates
 
diverse functionality
 
reactive electrophiles
 
reactivity
 
stoichiometric quantity
 
tetrafluoroborates