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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
Citation
Yang, Y and Canty, AJ and McKay, AI and Donnelly, PS and O'Hair, RAJ, Palladium-mediated CO2 extrusion followed by insertion of isocyanates for the synthesis of benzamides: translating fundamental mechanistic studies to develop a catalytic protocol, Organometallics, 39, (3) pp. 453-467. ISSN 0276-7333 (2020) [Refereed Article]
Copyright Statement
© 2020 American Chemical Society
DOI: doi:10.1021/acs.organomet.9b00820
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 Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | palladium catalysis, DFT, mass spectrometry, reaction mechanism, organic synthesis |
| Research Division: | Chemical Sciences |
| Research Group: | Inorganic chemistry |
| Research Field: | Transition metal chemistry |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding knowledge |
| Objective Field: | Expanding knowledge in the chemical sciences |
| UTAS Author: | Canty, AJ (Professor Allan Canty) |
| ID Code: | 137421 |
| Year Published: | 2020 |
| Web of Science® Times Cited: | 14 |
| Deposited By: | Chemistry |
| Deposited On: | 2020-02-12 |
| Last Modified: | 2022-08-19 |
| Downloads: | 0 |
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