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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
journal contribution
posted on 2023-05-20, 10:53 authored by Yang, Y, Allan CantyAllan Canty, McKay, AI, Donnelly, PS, O'Hair, RAJMechanistic 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.
History
Publication title
OrganometallicsVolume
39Pagination
453-467ISSN
0276-7333Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
© 2020 American Chemical SocietyRepository Status
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