4.5 Article

Visible Light-Promoted Three-Component Carboazidation of Unactivated Alkenes with TMSN3 and Acrylonitrile

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 36, Issue 11, Pages 1017-1023

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800320

Keywords

alkene difunctionalization; visible light photocatalysis; three-component reaction; redox-neutral; organoazide; azidyl radical

Funding

  1. NSFC [21472162]
  2. National Basic Research Program of China [2015CB856600]
  3. Fundamental Research Funds for the Central Universities of China [2018QNA3009]
  4. Thousand Youth Talents Plan
  5. Zhejiang University

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A novel difunctionalization of unactivated alkenes has been reported via visible light-promoted three-component carboazidation using TMSN3 and acrylonitrile as partners without any stoichiometric oxidants. This protocol is operationally simple for straightforward access to azido derivatives with good functional group tolerance from readily available starting materials. A facile azido radical-catalyzed [3+2] cycloaddition reaction of vinylcyclopropane with acrylonitrile was also observed to deliver a multi-substituted cyclopentane.

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