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

Org Lett. 2010 Oct 1;12(19):4388-91. doi: 10.1021/ol1018739.

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.

MeSH terms

  • Catalysis
  • Mesylates / chemical synthesis*
  • Molecular Structure
  • Palladium / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Temperature

Substances

  • Mesylates
  • Quaternary Ammonium Compounds
  • methyl triflate
  • Palladium