Iron-Catalysed Carbene Transfer to Isocyanides as a Platform for Heterocycle Synthesis
| Autor: | Thomas R. Roose, H. Daniel Preschel, Helena Mayo Tejedor, Jasper C. Roozee, Trevor A. Hamlin, Bert U. W. Maes, Eelco Ruijter, Romano V. A. Orru |
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| Přispěvatelé: | AMIBM, RS: FSE AMIBM, Organic Chemistry, AIMMS, Theoretical Chemistry, Chemistry and Pharmaceutical Sciences |
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Chemistry: a European journal. Wiley-VCH Verlag Chemistry-A European Journal, 29(9):e202203074. Wiley-VCH Verlag Chemistry: a European journal Roose, T R, Preschel, H D, Mayo Tejedor, H, Roozee, J C, Hamlin, T A, Maes, B U W, Ruijter, E & Orru, R V A 2023, ' Iron-Catalysed Carbene Transfer to Isocyanides as a Platform for Heterocycle Synthesis ', Chemistry-A European Journal, vol. 29, no. 9, e202203074 . https://doi.org/10.1002/chem.202203074 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.202203074 |
| Popis: | An iron-catalysed carbene transfer reaction of diazo compounds to isocyanides has been developed. The resulting ketenimines are trapped in situ with various bisnucleophiles to access a range of densely functionalized heterocycles (pyrimidinones, dihydropyrazolones, 1H-tetrazoles) in a one-pot process. The electron-rich Hieber anion ([Fe(CO) 3NO] −) facilitates efficient catalytic carbene transfer from acceptor-type α-diazo carbonyl compounds to isocyanides, providing a cost-efficient and benign alternative to similar noble metal-catalysed processes. Based on DFT calculations a plausible reaction mechanism for activation of the α-diazo carbonyl carbene precursor and ketenimine formation is provided. |
| Databáze: | OpenAIRE |
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