Modular synthesis of azines bearing a guanidine core from N‐heterocyclic carbene (NHC)‐derived selenoureas and diazo reagents
- Author
- Efstathios Tonis, Nikolaos Tzouras, Nestor Bracho Pozsoni (UGent) , Marina Saab, Subhrajyoti Bhandary (UGent) , Kristof Van Hecke (UGent) , David J. Nelson, Fady Nahra (UGent) , Steven Nolan (UGent) and Georgios C. Vougioukalakis
- Organization
- Project
-
- Unsymmetrical Strategies in Dual Gold Catalysis: Fine-tuning and Bottom-up Design of Catalytic Systems
- Gold Photocatalysis (PhotAuCat)
- Dioxide to Monoxide (D2M): Innovative catalysis for CO2 to CO conversion
- Catalysts for Carbon Circularity: Innovative chemistry for upgrading plastic waste (C3)
- BOF-ZAP-ambt in homogene katalyse en organometaalchemie
- Metal-N-Heterocyclic carbene complexes as catalysts in borylation catalysis.
- 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, alpha-diazoesters, alcohols, and triphenylphosphine was also developed, providing highly functionalized azines.
- Keywords
- N-heterocyclic carbene-derived selenoureas, Diazo compounds, Azine-guanidine derivatives, Aza-Wittig type reaction, Phosphine-mediated transformation, AZA-WITTIG REACTION, NMR-SPECTROSCOPY, SELECTIVE SYNTHESIS, FACILE SYNTHESIS, BOND FORMATION, CHEMISTRY, COMPLEXES, ACCESS, BASE, 2,2,2-TRIFLUORODIAZOETHANE
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01JNGNCDDNY13F0KZEHPRYRKK2
- MLA
- Tonis, Efstathios, et al. “Modular Synthesis of Azines Bearing a Guanidine Core from N‐heterocyclic Carbene (NHC)‐derived Selenoureas and Diazo Reagents.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 30, no. 53, 2024, doi:10.1002/chem.202401816.
- APA
- Tonis, E., Tzouras, N., Bracho Pozsoni, N., Saab, M., Bhandary, S., Van Hecke, K., … Vougioukalakis, G. 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). https://doi.org/10.1002/chem.202401816
- Chicago author-date
- Tonis, Efstathios, Nikolaos Tzouras, Nestor Bracho Pozsoni, Marina Saab, Subhrajyoti Bhandary, Kristof Van Hecke, David J. Nelson, Fady Nahra, Steven Nolan, and Georgios C. Vougioukalakis. 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). https://doi.org/10.1002/chem.202401816.
- Chicago author-date (all authors)
- Tonis, Efstathios, Nikolaos Tzouras, Nestor Bracho Pozsoni, Marina Saab, Subhrajyoti Bhandary, Kristof Van Hecke, David J. Nelson, Fady Nahra, Steven Nolan, and Georgios C. Vougioukalakis. 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). doi:10.1002/chem.202401816.
- Vancouver
- 1.Tonis E, Tzouras N, Bracho Pozsoni N, Saab M, Bhandary S, Van Hecke K, et al. Modular synthesis of azines bearing a guanidine core from N‐heterocyclic carbene (NHC)‐derived selenoureas and diazo reagents. CHEMISTRY-A EUROPEAN JOURNAL. 2024;30(53).
- IEEE
- [1]E. Tonis et al., “Modular synthesis of azines bearing a guanidine core from N‐heterocyclic carbene (NHC)‐derived selenoureas and diazo reagents,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 30, no. 53, 2024.
@article{01JNGNCDDNY13F0KZEHPRYRKK2,
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, alpha-diazoesters, alcohols, and triphenylphosphine was also developed, providing highly functionalized azines.}},
articleno = {{e202401816}},
author = {{Tonis, Efstathios and Tzouras, Nikolaos and Bracho Pozsoni, Nestor and Saab, Marina and Bhandary, Subhrajyoti and Van Hecke, Kristof and Nelson, David J. and Nahra, Fady and Nolan, Steven and Vougioukalakis, Georgios C.}},
issn = {{0947-6539}},
journal = {{CHEMISTRY-A EUROPEAN JOURNAL}},
keywords = {{N-heterocyclic carbene-derived selenoureas,Diazo compounds,Azine-guanidine derivatives,Aza-Wittig type reaction,Phosphine-mediated transformation,AZA-WITTIG REACTION,NMR-SPECTROSCOPY,SELECTIVE SYNTHESIS,FACILE SYNTHESIS,BOND FORMATION,CHEMISTRY,COMPLEXES,ACCESS,BASE,2,2,2-TRIFLUORODIAZOETHANE}},
language = {{eng}},
number = {{53}},
pages = {{10}},
title = {{Modular synthesis of azines bearing a guanidine core from N‐heterocyclic carbene (NHC)‐derived selenoureas and diazo reagents}},
url = {{http://doi.org/10.1002/chem.202401816}},
volume = {{30}},
year = {{2024}},
}
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