4.6 Article

Selective oxygenation of alkynes: a direct approach to diketones and vinyl acetate

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 48, Pages 9909-9913

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01404a

Keywords

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Funding

  1. National Science Foundation [NSF 21402066]
  2. Fundamental Research Funds for the Central Universities [JUSRP11419]
  3. Natural Science Foundation of Jiangsu Province [SBK201222312, BK20140139]
  4. MOESAFEA [B13025]

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Arylalkynes can be converted into alpha-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)(2) as an oxidant at room temperature. A series of substituted alpha-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes.

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