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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
journal contribution
posted on 2023-05-21, 00:45 authored by Altalhi, WAO, McKay, AI, Spyrou, B, Allan CantyAllan Canty, Donnelly, PS, O'Hair, RAJKey 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.
History
Publication title
Journal of Organometallic ChemistryVolume
950Article number
121973Number
121973Pagination
1-9ISSN
0022-328XDepartment/School
School of Natural SciencesPublisher
Elsevier Science SaPlace of publication
Po Box 564, Lausanne, Switzerland, 1001Rights statement
© 2021 Elsevier B.V.Repository Status
- Restricted