4.8 Article

Iron-Catalyzed Radical Acyl-Azidation of Alkenes with Aldehydes: Synthesis of Unsymmetrical β-Azido Ketones

Journal

ORGANIC LETTERS
Volume 21, Issue 1, Pages 256-260

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03688

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Funding

  1. National Key R&D Program of China [2017YFA0700103]
  2. NSFC [21502191, 21672213, 21871258]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Haixi Institute of CAS [CXZX-2017-P01]

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An iron-catalyzed acyl-azidation of alkenes under mild reaction conditions has been developed. Aromatic aldehydes or aliphatic aldehydes can be used as the acyl radical precursors; TMSN3 is used as the azido source; TBHP is the initiator. The synthesized unsymmetrical beta-azido ketones can be easily transformed into valuable functionalized compounds, such as gamma-aminol, gamma-azido alcohol, beta-azido oxime, beta-azido ester, and triazoles.

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