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Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes
Ping, Lucy,Bak, JungMin,Kim, Youngmee,Bouffard, Jean American Chemical Society 2018 Journal of organic chemistry Vol.83 No.16
<P>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 <I>p</I>- and <I>o</I>-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-<I>tert</I>-alkylated diphenoquinones in NHC-based oxidative transformations.</P> [FIG OMISSION]</BR>