Coumaraz-2-on-4-ylidene: Ambiphilic N-Heterocyclic Carbenes with a Tunable Electronic Structure

Angewandte Chemie
Hayoung SongEunsung Lee

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 77 Se 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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Citations

Jul 31, 2018·Chemistry : a European Journal·Youngsuk Kim, Eunsung Lee
Oct 1, 2019·Chemical Communications : Chem Comm·M Brenton Gildner, Todd W Hudnall
Aug 29, 2019·Angewandte Chemie·Prakash R SultaneChristopher W Bielawski
Nov 11, 2020·Chemistry : a European Journal·Hyunho KimEunsung Lee
Jul 13, 2021·Chemistry, an Asian Journal·Hayoung Song, Eunsung Lee

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