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Chemoselective Intermolecular α-Arylation of Amides

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Peng,  Bo
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Farès,  C.
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Maulide,  N.
Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria);
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Peng, B., Geerdink, D., Farès, C., & Maulide, N. (2014). Chemoselective Intermolecular α-Arylation of Amides. Angewandte Chemie International Edition, 53(21), 5462-5466. doi:10.1002/anie.201402229.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-4B20-1
Abstract
A new approach for the fully chemoselective α-arylation of amides is presented. By means of electrophilic amide activation, aryl groups can be regioselectively introduced α- to amides, even in the presence of esters and alkyl ketones. Mechanistic studies reveal key reaction intermediates and emphasize a remarkably subtle base effect in this transformation.