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
Author(s)
Hayoung Song; Hyunho Kim; EunSung Lee
Publication Date
2018-07
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.28, pp.8603 - 8607
Publisher
WILEY-V C H VERLAG GMBH
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. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei
URI
https://pr.ibs.re.kr/handle/8788114/4959
ISSN
1433-7851
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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