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Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

ABSTRACT: 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.

SUBMITTER: Waetzig SR

PROVIDER: S-EPMC2707754 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

Waetzig Shelli R SR Tunge Jon A JA

Journal of the American Chemical Society 20071108 48

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 heteroc ...[more]

PMID: 17988134

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