Palladium-Catalyzed Condensation of Aryl Halides with Phenylsulfonylacetonitrile and Diethyl Cyanomethylphosphonate

Takao Sakamoto, Eisaku Katoh, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

The palladium(0)-catalyzed condensation of aryl halides with the sodium salts of phenylsulfonylacetonitrile and diethyl cyanomethylphosphonate in dimethoxyethane gave the corresponding α-phenylsulfonylareneacetonitriles and diethyl arylcyanomethylphosphonates in good yields. The α-phenylsulfonylareneacetonitriles were easily desulfonylated with zinc to give the areneacetonitriles, and the arylcyanomethylphosphonates were converted to the alkylideneareneacetonitriles by means of the Horner-Emmons reaction.

Original languageEnglish
Pages (from-to)1513-1517
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume38
Issue number6
DOIs
Publication statusPublished - 1990

Keywords

  • Horner-Emmons reaction
  • aryl halide
  • desulfonylation
  • diethyl cyanomethylphosphonate
  • palladium-catalyzed reaction
  • phenylsulfonylacetonitrile
  • zinc dust

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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