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Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes
- Title
- Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes
- Authors
- Ping, Lucy; Bak, JungMin; Kim, Youngmee; Bouffard, Jean
- Ewha Authors
- 김영미; Jean Bouffard
- SCOPUS Author ID
- 김영미; Jean Bouffard
- Issue Date
- 2018
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- ISSN
- 0022-3263
- Citation
- JOURNAL OF ORGANIC CHEMISTRY vol. 83, no. 16, pp. 9240 - 9249
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- 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.
- DOI
- 10.1021/acs.joc.8b01236
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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