Coumaraz-2-on-4-ylidene: Ambiphilic N-Heterocyclic Carbenes with a Tunable Electronic Structure
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- Title
- Coumaraz-2-on-4-ylidene: Ambiphilic N-Heterocyclic Carbenes with a Tunable Electronic Structure
- Authors
- Song, Hayoung; Kim, Hyunho; Lee, Eunsung
- Date Issued
- 2018-07
- Publisher
- John Wiley & Sons Ltd.
- Abstract
- Herein, a coumaraz-2-on-4-ylidene (1) as a new example of an ambiphilic N-heterocyclic carbene, having electronic properties that can be fine-tuned, is reported. The N-carbamic and aryl groups on the carbene carbon center provide exceptionally high electrophilicity and nucleophilicity simultaneously to the carbene center, as evidenced by the Se-77 NMR chemical shifts of their selenoketone derivatives and the CO stretching strengths of their rhodium carbonyl complexes. Since the precursors of 1 could be synthesized from various functionalized Schiff bases in a practical and scalable manner, the electronic properties of 1 can be fine-tuned in a quantitative and predictable way by using the Hammett sigma constant of the functional groups on aryl ring. The facile electronic tuning capability of 1 may be applicable to eliciting novel properties in main-group and transition-metal chemistry.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/99271
- DOI
- 10.1002/anie.201804249
- ISSN
- 1433-7851
- Article Type
- Article
- Citation
- Angewandte Chemie - International Edition, vol. 57, no. 28, page. 8603 - 8607, 2018-07
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