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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
- Abstract
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 77Se 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 σ 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.
- Subjects
CARBENES; ELECTRONIC structure; NUCLEAR magnetic resonance spectroscopy; CHEMICAL shift (Nuclear magnetic resonance); SCHIFF bases
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 28, p8739
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201804249