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Iron‐Catalysed Carbene Transfer to Isocyanides as a Platform for Heterocycle Synthesis
Author(s) -
Roose Thomas R.,
Preschel H. Daniel,
Mayo Tejedor Helena,
Roozee Jasper C.,
Hamlin Trevor A.,
Maes Bert U. W.,
Ruijter Eelco,
Orru Romano V. A.
Publication year - 2023
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202203074
Subject(s) - carbene , diazo , ketenimine , chemistry , combinatorial chemistry , catalysis , photochemistry , medicinal chemistry , organic chemistry
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, 1 H ‐tetrazoles) in a one‐pot process. The electron‐rich Hieber anion ([Fe(CO) 3 NO] − ) 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.