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 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.
Waetzig
Shelli R
SR
Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Tunge
Jon A
JA
D019342:Acetic Acid / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D004952:Esters / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D004952:Esters; D008024:Ligands; D009578:Nitrobenzenes; D010165:Palladium; C036077:nitrobenzene; D019342:Acetic Acid