We thank the Fonds der Chemischen Industrie, the European Research Council (ERC), and the Deutsche Forschungsgemeinschaft (DFG) for financial support. We also thank BASF AG (Ludwigshafen), Chemetall GmbH (Frankfurt), and Heraeas (Hanau) for generous gifts of chemicals.
Lewis Acid Promoted Benzylic Cross-Couplings of Pyridines with Aryl Bromides†
Article first published online: 30 JUN 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 33, pages 7686–7690, August 8, 2011
How to Cite
Duez, S., Steib, A. K., Manolikakes, S. M. and Knochel, P. (2011), Lewis Acid Promoted Benzylic Cross-Couplings of Pyridines with Aryl Bromides. Angew. Chem. Int. Ed., 50: 7686–7690. doi: 10.1002/anie.201103074
- Issue published online: 5 AUG 2011
- Article first published online: 30 JUN 2011
- Manuscript Received: 4 MAY 2011
- Fonds der Chemischen Industrie
- European Research Council (ERC)
- Deutsche Forschungsgemeinschaft (DFG)
Either ZnCl2, Sc(OTf)3 , or BF3⋅OEt2 can promote the palladium-catalyzed arylation of methylpyridines and related heterocycles (see example). The complexation of the Lewis acid to the nitrogen atom in the heterocycle facilitates the reductive elimination, leading to various arylated pyridines in high yields. BF3⋅OEt2 was also found to promote highly regioselective metalations in the case of 2,4-lutidine.