4.7 Article

Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 16, Pages 10719-10727

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01253

Keywords

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Funding

  1. Outstanding Youth Project of Guangdong Natural Science Foundation [2020B1515020026]
  2. Innovation and Strong School Project of Guangdong Pharmaceutical University [2015cxqx212, 2018KQNCX131]
  3. Science and Technology Planning Project of Guangdong Province [201806040009, 201804010349]
  4. National Special Fund for Agro-scientific Research in the Public Interest of China [201503112-8]
  5. National Key Research and Development Project [2017YFD0201600]
  6. Provincial Experimental Teaching Demonstration Center of Chemistry & Chemical Engineering
  7. Guangdong Cosmetics Engineering & Technology Research Center
  8. key disciplines construction from Guangdong and Zhongshan cooperating

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A range of indolizine smoothly underwent visible-light-induced intermolecular [3+2] annulations with internal alkynes to afford pyrrolo[2,1,5-cd]indolizine in good to excellent yields with high regioselectivity. Through this cascade reaction, a series of fluoroactive fused indolizines with a large pi-system were conveniently synthesized. The usage of visible light as energy source with air as a stoichiometric oxidant under simple conditions makes this process attractive and practical.

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