Interaction of acyl chlorides and triethylsilane catalysed by cis-di-chlorobis(triphenylphosphine)platinum(II) and related complexes

Abstract

The acyl halides XC₆H₄COCl (X = H, p-Me, o-MeO, p-MeO, p-Cl, p-Br, and p-NO₂) are converted into the aldehydes XC₆H₄CHO in 50–84% yield on treatment with triethylsilane at 120 °C in the presence of a 1 × 10^–3 molar proportion of cis-[PtCl₂(PPh₃)₂]. Cinnamoyl and n-pentanoyl chloride give the corresponding aldehydes in 65 and 20% yield, respectively. A more detailed study using p-methoxybenzoyl chloride has shown that triethyl-p-methoxybenzyloxysilane is also formed, by further reaction of the aldehyde with the triethylsilane. The conversion of this chloride into aldehyde is also catalysed by cis-[PdCl₂(PPh₃)₂], [RuCl₂(PPh₃)₃], and trans-[IrCl(CO)(PPh₃)₂], and, except for catalysis by the iridium complex, the benzyloxysilane is also formed.