Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air

Kazutaka Matoba, Shin Ichi Motofusa, Chan Sik Cho, Kouichi Ohe, Sakae Uemura

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Abstract

Diphenylantimony chloride and phenylantimony dichloride, mainly the former, react smoothly with alkenes in acetonitrile at r.t. in the presence of a catalytic amount of Pd(OAc)2 under air to afford the corresponding phenylated alkenes (Heck-type reaction). The addition of AgOAc as reoxidant is not necessary for this reaction in sharp contrast to similar reactions using triarylstibines. The oxygen absorption is confirmed in this catalytic reaction and the reaction does not proceed catalytically in palladium(II) under inert gases, such as nitrogen or argon. Even under air the addition of a radical scavenger stopped the reaction. The regeneration of PhPdOAc species from Ph2SbCl, HPdOAc species and oxygen is proposed as a key step in the catalytic cycle where oxygen-containing radical species might be present as intermediates.

Original languageEnglish
Pages (from-to)3-10
Number of pages8
JournalJournal of Organometallic Chemistry
Volume574
Issue number1
DOIs
StatePublished - 8 Feb 1999

Keywords

  • Antimony
  • Heck reaction
  • Oxygen
  • Palladium

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