Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters
Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters
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DOI：
10.1021/ja077070r
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发表时间：
2007-12-05
影响因子：
15
通讯作者：
Tunge, Jon A.
中科院分区：
文献类型：
--
作者：
Waetzig, Shelli R.;Tunge, Jon A.
硝基苯乙酸的烯丙酯进行容易的钯催化脱羧偶联。单-和二硝基芳烃底物都给出了高产率的偶联产物。此外，反应的速率表明，脱羧是限速的和底物，空间不利于实现的反应构象脱羧是不可行的。最后，产物硝基芳烃还原为相应的苯胺提供了获得包括喹啉和二氢喹诺酮在内的各种杂环的途径。
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.