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- Title
Thiazol-2-ylidenes as N-Heterocyclic carbene ligands with enhanced electrophilicity for transition metal catalysis.
- Authors
Zhang, Jin; Li, Tao; Li, Xiangyang; Lv, Anqi; Li, Xue; Wang, Zheng; Wang, Ruihong; Ma, Yangmin; Fang, Ran; Szostak, Roman; Szostak, Michal
- Abstract
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. N-heterocyclic carbenes are widely exploited as ligands in transition metal catalysis, but are largely limited to N-arylimidazolylidenes. Here, the authors report on the steric and electronic properties of thiazol-2-ylidenes, demonstrating that their enhanced π-electrophilicity makes them attractive as carbene ligands in transition metal-catalysed electrophilic cyclization reactions.
- Subjects
TRANSITION metals; LIGANDS (Chemistry); COORDINATE covalent bond; PHARMACEUTICAL chemistry; CATALYSIS
- Publication
Communications Chemistry, 2022, Vol 5, Issue 1, p1
- ISSN
2399-3669
- Publication type
Article
- DOI
10.1038/s42004-022-00675-7