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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

Altalhi, WAO, McKay, AI, Spyrou, B, Canty, AJ, Donnelly, PS and O'Hair, RAJ 2021 , '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, vol. 950 , pp. 1-9 , doi: 10.1016/j.jorganchem.2021.121973.

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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 Type: Article
Authors/Creators:Altalhi, WAO and McKay, AI and Spyrou, B and Canty, AJ and Donnelly, PS and O'Hair, RAJ
Keywords: C-H bond functionalisation, amidation, catalysis, mass spectrometry, density functional theory, cyclometalation, ruthenium, organoruthenium
Journal or Publication Title: Journal of Organometallic Chemistry
Publisher: Elsevier Science Sa
ISSN: 0022-328X
DOI / ID Number: 10.1016/j.jorganchem.2021.121973
Copyright Information:

© 2021 Elsevier B.V.

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