• Title/Summary/Keyword: $\alpha$-Keto (cyanomethylene)triphenylphosphorane

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A Versatile Synthesis of α-Keto (cyanomethylene)triphenylphosphorane Ylides from Alkyl Halides Utilizing a Noble Phenylsulfonyl Reagent

  • Lee, Kieseung;Hwang, Chan-Yeon
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.2953-2958
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    • 2013

  • A noble phenylsulfonyl reagent 8 having ${\alpha}$-oxo (cyanomethylene)triphenylphosphorane ylide subunit readily condensed with various alkyl halides under basic conditions to afford ${\beta}$-alkyl-${\alpha}$-oxo-${\beta}$-phenylsulfonyl (cyanomethylene)triphenylphosphorane ylides 9 in excellent yields. These sulfonyl ylides 9 were then reductively desulfonylated with $Na(Hg)/Na_2HPO_4$ in the presence of methanol to provide ${\alpha}$-keto (cyanomethylene)-triphenylphosphorane ylides 2' in good to excellent yields. Our new synthetic approach offers an expeditious access to various ${\alpha}$-keto (cyanomethylene)triphenylphosphorane ylides from alkyl halides utilizing a new phenylsulfonyl reagent as the key reagent under mild reaction conditions in good overall yields.

  • https://doi.org/10.5012/bkcs.2013.34.10.2953 인용 PDF KSCI