The promoted Tishchenko reaction and catalytic intermediate by 2-aminopyrrolyl dilithium compounds

•A simple and efficient catalytic system for Tishchenko reaction is presented.•The redox reaction between aminopyrrolyl lithium and aldehyde was reported firstly.•The initiated intermediate was characterized by NMR, elemental analysis and X-ray study.

The dimerization of aldehydes to the analogous carboxylic esters (Tischenko reaction) has been achieved in impressive yields using the dilithium compounds containing bidentate di-anionic pyrrolyl ligands as initiators. The initiated intermediate {[2-(tBuNCH)C4H3NLi][PhCH2OLi(TMEDA)]}2 was isolated and characterized by satisfactory C, H and N microanalysis, 1H, 13C{1H} and 7Li NMR spectra in pyridine-d5 at ambient temperature, and single crystal X-ray structural data. The processes involve a redox reaction of 2-aminopyrrolyl dilithium compound with aldehyde.

Graphical abstractThe dimerization of aldehydes (Tischenko reaction) has been achieved in impressive yields using 2-aminopyrrolyl dilithium compounds as initiators. The initiated intermediate {[2-(tBuNCH)C4H3NLi][PhCH2OLi(TMEDA)]}2 was isolated and characterized by microanalysis, NMR spectra and single crystal X-ray structural data. The processes involve a redox reaction of 2-aminopyrrolyl dilithium compound with aldehyde.Figure optionsDownload full-size imageDownload as PowerPoint slide