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Room Temperature Palladium-Catalyzed Cross Coupling of Aryltrimethylammonium Triflates with Aryl Grignard Reagents

Jonathan T. Reeves*, Daniel R. Fandrick, Zhulin Tan, Jinhua J. Song, Heewon Lee, Nathan K. Yee and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email: jonathan.reevesboehringer-ingelheim.com

J. T. Reeves, D. R. Fandrick, Z. Tan, J. J. Song, H. Lee, N. K. Yee, C. H. Senanayake, Org. Lett., 2010, 12, 4388-4391.

DOI: 10.1021/ol1018739 (free Supporting Information)


Abstract

Aryltrimethylammonium triflates and tetrafluoroborates are highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling proceeds at ambient temperature with a nearly stoichiometric quantity of Grignard reagent and tolereates diverse functionality.

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Key Words

Cross Coupling, Kumada Coupling


ID: J54-Y2010-2760