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

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...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 48; pp. 14860 - 14861
Main Authors Waetzig, Shelli R, Tunge, Jon A
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 05.12.2007
Subjects
Acetic Acid - chemistry
Catalysis
Decarboxylation
Esters - chemistry
Ligands
Molecular Structure
Nitrobenzenes - chemistry
Palladium - chemistry
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Summary: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.
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ark:/67375/TPS-DVK09DCS-B
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja077070r