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Examination of N,N-dimethylbenzylamine as a substrate for ruthenium-catalysed C-H (thio)amidation: A mass spectrometry and DFT directed study
Citation
Altalhi, WAO and McKay, AI and Spyrou, B and Canty, AJ and Donnelly, PS and O'Hair, RAJ, Examination of N,N-dimethylbenzylamine as a substrate for ruthenium-catalysed C-H (thio)amidation: A mass spectrometry and DFT directed study, Journal of Organometallic Chemistry, 950 Article 121973. ISSN 0022-328X (2021) [Refereed Article]
Copyright Statement
© 2021 Elsevier B.V.
DOI: doi:10.1016/j.jorganchem.2021.121973
Abstract
Key steps in the potential application of N,N-dimethylbenzylamine, a widely used substrate in organometallic chemistry, in ruthenium-catalysed C-H (thio)amidation have been examined. In particular, a cationic cyclometalated ruthenium(II) complex has been synthesised and characterised by X-ray crystallography and its insertion reactions with phenyl iso(thio)cyanate studied using electrospray ionisation high-resolution mass spectrometry (ESI-HRMS) and Density Functional Theory (DFT) calculations. The ruthenium(II) catalysed process proved to be inferior to synthesising (thio)amides by ortho-lithiation, iso(thio)cyanate insertion hydrolysis, and provide insights into mechanisms that are consistent with proposals reported in examination of 2-phenylpyridine as the substrate.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | C-H bond functionalisation, amidation, catalysis, mass spectrometry, density functional theory, cyclometalation, ruthenium, organoruthenium |
| 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: | 145320 |
| Year Published: | 2021 |
| Deposited By: | Chemistry |
| Deposited On: | 2021-07-15 |
| Last Modified: | 2021-09-02 |
| Downloads: | 0 |
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