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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
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