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

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

Organic letters (2010-09-04)
Jonathan T Reeves, Daniel R Fandrick, Zhulin Tan, Jinhua J Song, Heewon Lee, Nathan K Yee, Chris H Senanayake
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl trifluoromethanesulfonate, ≥98%