Coumaraz‐2‐on‐4‐ylidene: Ambiphilic N‐Heterocyclic Carbenes with a Tunable Electronic Structure |
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Authors: | Hayoung Song Hyunho Kim Prof. Eunsung Lee |
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Affiliation: | 1. Center for Self-assembly and Complexity, Institute for Basic Science (IBS), Pohang, Republic of Korea;2. Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, Republic of Korea;3. Division of Advanced Materials Science, Pohang University of Science and Technology (POSTECH), Pohang, Republic of Korea |
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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. |
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Keywords: | carbenes ligand design main-group elements synthetic methods transition metals |
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