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, 30 (53). e202401816. ISSN 1521-3765 (https://doi.org/10.1002/chem.202401816)

[thumbnail of Tonis-etal-CAEJ-2024-Modular-synthesis-of-azines-bearing-a-guanidine-core-from-N-Heterocyclic-carbene] Text. Filename: Tonis-etal-CAEJ-2024-Modular-synthesis-of-azines-bearing-a-guanidine-core-from-N-Heterocyclic-carbene.pdf
Accepted Author Manuscript
Restricted to Repository staff only until 1 January 2099.
Download (2MB) | Request a copy

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.

ORCID iDs

Tonis, Efstathios, Tzouras, Nikolaos V., Pozsoni, Nestor Bracho, Saab, Marina, Bhandary, Subhrajyoti, Van Hecke, Kristof, Nelson, David J. ORCID logoORCID: https://orcid.org/0000-0002-9461-5182, Nahra, Fady, Nolan, Steven P. and Vougioukalakis, Georgios C.;
  • Item type:Article
    ID code:90019
    Dates:
    Date
    Event
    19 September 2024
    Published
    11 July 2024
    Published Online
    11 July 2024
    Accepted
    9 May 2024
    Submitted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:24 Jul 2024 12:04
    Last modified:11 Nov 2024 14:24
    URI:https://strathprints.strath.ac.uk/id/eprint/90019
CORE (COnnecting REpositories)