4.7 Article

Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones

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JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 23, 页码 16409-16424

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01763

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  1. Spanish Ministerio de Economia, Industria y Competitividad (MINEICO) [AGL2017-88083-R]
  2. Junta de Andalucia [FQM-169]
  3. Servicio Central de Investigacion en Ciencia y Tecnologia of the University of Cadiz

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The study utilized microwave irradiation to promote the oxyphosphorylation of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)(4)]BF4, yielding different phosphonylated indenones.
Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)(4)]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding beta-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.

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