PdCl2-catalyzed hydrogenolysis of an Ar-Cl bond by sodium phosphinate in an aqueous alkaline medium

The hydrogenolysis of the Ar-Cl bond in chlorinated benzoic acids, anilines, and nitrogen-containing heterocycles by the action of NaH₂PO₂ in the presence of catalytic amounts of PdCl₂ and NaOH in an aqueous medium was studied. Under these conditions aryl chlorides were quantitatively converted into the corresponding arenes. Chloropyridines, such as 2-chloropyridine and 3, 5-dichloropicolinic acid, did not undergo hydrogenolysis even in the presence of an equivalent amount of NaI. A distinctortho effect was observed forortho-substituted substrates.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 607–609, March, 1993.