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Palladium-mediated CO2 extrusion followed by insertion of isocyanates for the synthesis of benzamides: translating fundamental mechanistic studies to develop a catalytic protocol

Yang, Y, Canty, AJ, McKay, AI, Donnelly, PS and O'Hair, RAJ 2020 , 'Palladium-mediated CO2 extrusion followed by insertion of isocyanates for the synthesis of benzamides: translating fundamental mechanistic studies to develop a catalytic protocol' , Organometallics, vol. 39, no. 3 , pp. 453-467 , doi: 10.1021/acs.organomet.9b00820.

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Abstract

Mechanistic studies of a stoichiometric palladium-mediated ExIn (ExIn = extrusion–insertion) decarboxylative amidation of aromatic carboxylic acids are presented, providing gas-phase and condensed-phase spectroscopic data, as well as theoretical computational evidence for intermediates in a proposed stepwise process. The understanding gained from these mechanistic studies directed the development of a palladium-catalyzed procedure in which benzamides are obtained in good to high yields in a one-pot 30 min microwave irradiation assisted protocol. A combination of experimental data and DFT calculations reveals that certain ligand additives favor the selective formation of benzamides rather than the undesired protodecarboxylation side product.

Item Type: Article
Authors/Creators:Yang, Y and Canty, AJ and McKay, AI and Donnelly, PS and O'Hair, RAJ
Keywords: palladium catalysis, DFT, mass spectrometry, reaction mechanism, organic synthesis
Journal or Publication Title: Organometallics
Publisher: Amer Chemical Soc
ISSN: 0276-7333
DOI / ID Number: 10.1021/acs.organomet.9b00820
Copyright Information:

© 2020 American Chemical Society

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