Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes
- 주제(기타) Chemistry, Organic
- 설명문(일반) [Ping, Lucy; Bak, JungMin; Kim, Youngmee; Bouffard, Jean] Ewha Womans Univ, Dept Chem & Nano Sci BK Plus 21, Seoul 03760, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000156544
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acs.joc.8b01236
초록/요약
Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push pull furanolactone chromophores, NHC fulvalenes, and a-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.
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