Iron-catalysed carbene transfer to isocyanides as a platform for heterocycle synthesis

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)(3)NO](-)) facilitates efficient catalytic carbene transfer from acceptor-type alpha-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 alpha-diazo carbonyl carbene precursor and ketenimine formation is provided.

Jaar van publicatie:2023

Trefwoorden:A1 Journal article

Toegankelijkheid:Open