Wydział Chemii

Jin Zhang

Tao Li

Xiangyang Li

Anqi Lv

Xue Li

Zheng Wang

Ruihong Wang

Yangmin Ma

Ran Fang

Roman Szostak

Michal Szostak

2022

Communications Chemistry

5

60/1-60/11

10.1038/s42004-022-00675-7

Naukowa

Angielski

Artykuł

Over the last 20 years, N-heterocyclic carbenes (NHCs) have emerged as a dominant direction in ligand development in transition metal catalysis. In particular, strong σ-donation in combination with tunable steric environment make NHCs to be among the most common ligands used for C–C and C–heteroatom bond formation. Herein, we report the study on steric and electronic properties of thiazol-2-ylidenes. We demonstrate that the thiazole heterocycle and enhanced π-electrophilicity result in a class of highly active carbene ligands for electrophilic cyclization reactions to form valuable oxazoline heterocycles. The evaluation of steric, electron-donating and π-accepting properties as well as structural characterization and coordination chemistry is presented. This mode of catalysis can be applied to late-stage drug functionalization to furnish attractive building blocks for medicinal chemistry. Considering the key role of N-heterocyclic ligands, we anticipate that N-aryl thiazol-2-ylidenes will be of broad interest as ligands in modern chemical synthesis.

Synthetic chemistry methodology, Organometallic chemistry, Structure elucidation

CC-BY

http://dx.doi.org/10.1038/s42004-022-00675-7

http://link.springer.com