Modular synthesis of azines bearing a guanidine core from N-Heterocyclic carbene (NHC)-derived selenoureas and diazo reagents
Tonis, Efstathios and Tzouras, Nikolaos V. and Pozsoni, Nestor Bracho and Saab, Marina and Bhandary, Subhrajyoti and Van Hecke, Kristof and Nelson, David J. and Nahra, Fady and Nolan, Steven P. and Vougioukalakis, Georgios C. (2024) Modular synthesis of azines bearing a guanidine core from N-Heterocyclic carbene (NHC)-derived selenoureas and diazo reagents. Chemistry- A European Journal. e202401816. ISSN 1521-3765 (https://doi.org/10.1002/chem.202401816)
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Abstract
N-Heterocyclic carbene (NHC)-derived selenoureas comprise a fundamentally important class of NHC derivatives, with key applications in coordination chemistry and the determination of NHC electronic properties. Considering the broad reactivity of chalcogen-containing compounds, it is surprising to note that the use of NHC-derived selenoureas as organic synthons remains essentially unexplored. The present contribution introduces a novel, straightforward transformation leading to azines bearing a guanidine moiety, through the reaction of a wide range of NHC-derived selenoureas with commercially available diazo compounds, in the presence of triphenylphosphine. This transformation offers a new approach to such products, having biological, materials chemistry, and organic synthesis applications. The guanidine-bearing azines are obtained in excellent yields, with all manipulations taking place in air. A reaction mechanism is proposed, based on both experimental mechanistic findings and density functional theory (DFT) calculations. A one-pot, multicomponent transesterification reaction between selenoureas, α-diazoesters, alcohols, and triphenylphosphine was also developed, providing highly functionalized azines. [Abstract copyright: © 2024 Wiley‐VCH GmbH.]
ORCID iDs
Tonis, Efstathios, Tzouras, Nikolaos V., Pozsoni, Nestor Bracho, Saab, Marina, Bhandary, Subhrajyoti, Van Hecke, Kristof, Nelson, David J.![ORCID logo](/images/orcid_16x16.png)
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Item type: Article ID code: 90019 Dates: DateEvent11 July 2024Published11 July 2024Published Online11 July 2024Accepted9 May 2024SubmittedSubjects:
Science > ChemistryDepartment: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 24 Jul 2024 12:04 Last modified: 29 Aug 2024 12:31 URI: https://strathprints.strath.ac.uk/id/eprint/90019