Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Lucy Ping, Jungmin Bak, Youngmee Kim, Jean Bouffard

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2 Scopus citations


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 α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.

Original languageEnglish
Pages (from-to)9240-9249
Number of pages10
JournalJournal of Organic Chemistry
Issue number16
StatePublished - 17 Aug 2018

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (Grant 2015R1D1A1A01059383). We thank Dr. Hea Kyoung Lee of the Organic Chemistry Research Center at Sogang University for ESI-MS analyses.

Publisher Copyright:
© 2018 American Chemical Society.


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