Journal article

Publication year: 2022

Pages: 1538-1541

Journal: Chemical Communications

Volume number: 58

Issue number: 10

ISSN: 1359-7345

DOI Link: https://doi.org/10.1039/d1cc05696d

Publisher: Royal Society of Chemistry

Abstract: 
We report the first preparation of N-alkoxyimidazolylidene (NOHC), a nucleophilic carbene based on an oxidized imidazolium core. The Arduengo-type analogous carbene center shows the most upfield C-13 NMR shift compared to common NHCs. The obtained gold(i) complex of the carbene follows the C-13 NMR upfield trend and shows the marked influence the alkoxy substituents. Similarly, the Se-77 and N-15 NMR shifts of a range of NOHC-selenium adducts show increased sigma-donation and decreased pi-back donation in the bonding with the nucleophile. This extension of the NHC family provides altered electronic properties for the use of such carbenes as ligands or catalysts.

Harvard Citation style: Bakhonsky, V., Becker, J., Mlostoń, G. and Schreiner, P. (2022) N-Alkoxyimidazolylidines (NOHCs): nucleophilic carbenes based on an oxidized imidazolium core, Chemical Communications, 58(10), pp. 1538-1541. https://doi.org/10.1039/d1cc05696d

APA Citation style: Bakhonsky, V., Becker, J., Mlostoń, G., & Schreiner, P. (2022). N-Alkoxyimidazolylidines (NOHCs): nucleophilic carbenes based on an oxidized imidazolium core. Chemical Communications. 58(10), 1538-1541. https://doi.org/10.1039/d1cc05696d