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Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high yields of the coupled products. Moreover, the rates of the reactions suggest that decarboxylation is rate-limiting and substrates that sterically disfavor attainment of the reactive conformation for decarboxylation are not viable. Finally, reduction of the product nitroarenes to the corresponding anilines provides access to a variety of heterocycles including quinolines and dihydroquinolones.

Palladium-Catalyzed Decarboxylative sp3−sp3 Coupling of Nitrobenzene Acetic Esters

Palladium-Catalyzed Decarboxylative sp³−sp³ Coupling of Nitrobenzene Acetic Esters