4.7 Article

Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/Annulation of N-Aryloxyacetamides with Alkynyloxiranes: Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans

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JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 16, 页码 9464-9470

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01166

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资金

  1. National Natural Science Foundation of China [21602167, 21402149]
  2. Natural Science Basic Research Plan in Shaanxi Province of China [2016JQ2019, 2015JQ2050]
  3. China Postdoctoral Science Foundation [2015M580830, 2014M550484, 2015T81013]
  4. Fundamental Research Funds for the Central Universities

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Alkynyloxiranes have been employed for the first time as effective coupling partners in Cp*Rh-III-catalyzed C-H functionalization reactions. Their annulation with N-aryloxyamides then offers a redox-neutral and efficient synthesis of functionalized 2,3-dihydrobenzofurans bearing an exocyclic E-allylic alcohol and a tetrasubstituted carbon center in good yields with a broad substrate scope. The products can be easily converted to molecules with more complexity, which provides an opportunity for rapid assembly of structurally diverse heterocycles.

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