Synthesis of Aromatic Carbonyl Compounds via Thallation-Carbonylation of Arenes

Article abstract of DOI:10.1021/ja00371a019

Simple arenes, substituted benzylic and β-phenylethyl alcohols, benzoic acid, phenylacetic acid, benzamide, acetanilide, phenylurea, and benzophenone have been thallated under variety of reaction conditions with thallium(III) trifluoroacetate and subsequently carbonylated with 19percent PdCl2, 2 equiv of LiCl, and MgO in either methanol or tetrahydrofuran under 1 atm of carbon monoxide to give aromatic esters, substituted phthalides and 3,4-dihydroisocoumarins, phthalic and homophthalic anhydride, phthalimide, and the ortho-substituted methyl esters of acetanilide, phenylurea, and benzophenone, respectively.The scope and limitations of this approach to aromatic carbonyl compounds are examined.