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Synfacts 2010(12): 1415-1415
DOI: 10.1055/s-0030-1258853
DOI: 10.1055/s-0030-1258853
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Cross-Coupling of Aryltrimethylammonium Triflates with Aryl Grignard Reagents
J. T. Reeves*, D. R. Fandrick, Z. Tan, J. J. Song, H. Lee, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Ridgefield, USA
Further Information
Publication History
Publication Date:
22 November 2010 (online)
Significance
A mild and general method for the cross-coupling of aryltrimethylammonium triflates with aryl organomagnesium reagents was developed. The reaction proceeds best under palladium catalysis at ambient temperature. Functional groups, such as ester functionalities, are well tolerated due to the fact that only a slight excess of Grignard reagent is used. Methylation of N,N-dimethylanilines and subsequent cross-coupling of the resulting aryltrimethylammonium triflate could be combined in a one-pot procedure leading to an increase in reaction times.