Palladium-catalyzed decarboxylative sp(3)-sp(3) 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 - 14862
Main Authors Waetzig, Shelli R., Tunge, Jon A.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.12.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CARBOXYLATES
OLEFINATION
ACIDS
ALLYLATION
ALKYL-HALIDES
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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.
Bibliography:Medline
NIH RePORTER
ISSN:0002-7863
DOI:10.1021/ja077070r