In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to give the corresponding aryl sulfides in excellent yield. The reaction is useful to prepare symmetrical or unsymmetrical diaryl sulfides and aryl alkyl sulfides. The reaction mechanism does not involve aryl halide radical anions, but is thought to involve oxidative addition of aryl halide to Pd(0), nucleophilic substitution on the adduct followed by reductive elimination.

Aryl bromide and iodide were found to react with aliphatic and aromatic thiolate anions to give the corresponding sulfides in the presence of Pd(O). The reaction was not inhibited by p-dinitrobenzene which is a good inhibitor for the SRN1.

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Alkohole (II) und das Nitrophenol (I) reagieren miteinander in Gegenwart von Azodicarbonsäurediethyl‐ ester (III) und Triphenylphosphin (IV) zu den aci‐Nitroestern (V), die mit dem Phosphorylid (VI) zu den substituierten Acrylsäureestern (VII) und dem p‐Benzochinonmonoxim (VIII) umgesetzt werden.