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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
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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 |
| Related URLs: | |
| Item Statistics: | View statistics for this item |
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