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

Lucy Ping, Jungmin Bak, Youngmee Kim, Jean Bouffard

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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 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
Volume83
Issue number16
DOIs
StatePublished - 17 Aug 2018

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