4.8 Article

Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes

Journal

ORGANIC LETTERS
Volume 18, Issue 15, Pages 3818-3821

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01830

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Funding

  1. National Science Foundation of China [21572027, 21372267]
  2. Postdoctoral Research Grant [2014M562278]

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A novel one-pot aryne transformation is described that affords various 4-quinolone derivatives without recourse to transition-metal catalysis. Arynes react with aza-Morita-Baylis-Hillman (AMBH) adducts through a cascade sequence involving an insertion/cyclization/ene reaction process to afford 4-quinolones in high yields with a broad substrate scope under mild reaction conditions. Essentially, an umpolung of reactivity at the beta carbon of alpha,beta-unsaturated ketone has been achieved by an inverse electron demand aryne-ene reaction to provide a C-arylated product.

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