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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, LucyBak, JungMinKim, YoungmeeBouffard, Jean
Ewha Authors
김영미Jean Bouffard
SCOPUS Author ID
김영미scopus; Jean Bouffardscopus
Issue Date
2018
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263JCR Link
Citation
JOURNAL OF ORGANIC CHEMISTRY vol. 83, no. 16, pp. 9240 - 9249
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS 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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