4.7 Article

Redox-Neutral Rhodium(III)-Catalyzed Chemospecific and Regiospecific [4+1] Annulation between Indoles and Alkenes for the Synthesis of Functionalized Imidazo[1,5-a]indoles

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JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 15, 页码 10591-10607

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01256

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资金

  1. Natural Science Foundation of Zhejiang Province [LY21B020003]
  2. National Natural Science Foundation of China [21602022]
  3. Chengdu Talents Program
  4. 1000 Talents Program of Sichuan Province
  5. Longquanyi District Talents Program
  6. Science and Technology Program of Sichuan Province [2018JY0345]
  7. Jinhua Branch of Sichuan Industrial Institute of Antibiotics [1003]
  8. Chengdu University New Faculty Start-up Fund [2081915037]

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This method utilizes internal alkenes embedded with an oxidizing function/leaving group as a rare onecarbon unit for a redox-neutral rhodium(III)-catalyzed chemo- and regiospecific [4+1] annulation, leading to the synthesis of functionalized imidazo[1,5-a]indoles with excellent chemo- and regioselectivity.
Exploiting internal alkenes embedded with an oxidizing function/leaving group as a rare and unconventional onecarbon unit, a redox-neutral rhodium(III)-catalyzed chemo- and regiospecific [4+1] annulation between indoles and alkenes for the synthesis of functionalized imidazo[1,5-a]indoles has been achieved. Internal alkenes employed here can fulfill an unusual [4+1] annulation rather than normal [4+2] annulation/C-H alkenylation. This method is characterized by excellent chemo- and regioselectivity, broad substrate scope, good functional group tolerance, good to high yields, and redox-neutral conditions.

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