School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, and Institute for Natural and Synthetic Organic Chemistry, Changzhou University , Changzhou 213164, P. R. China.
Org Lett. 2017 Aug 18;19(16):4319-4322. doi: 10.1021/acs.orglett.7b01989. Epub 2017 Aug 1.
Palladium-catalyzed multicomponent reactions (MCRs) between o-alkynylanlines, aryl iodides, and atmospheric pressure of CO are developed, affording a series of 3,3-diaryl 2,4-quinolinediones bearing a newly constructed quaternary carbon center in moderate to excellent yields. The reaction proceeded with a sequential carboxylation, trans-oxopalladation of C≡C bond by ArPdX species, and reductive elimination procedure leading to benzoxazine-2-ones bearing tetrasubstituted vinyl fragments. Then, rearrangement of benzoxazine-2-ones took place toward 3,3-diaryl 2,4-quinolinediones. This procedure features simultaneous formation of four bonds in one pot.
钯催化的邻炔基苯胺、芳基碘化物和常压 CO 之间的多组分反应（MCRs）得到了一系列 3,3-二芳基 2,4-喹啉二酮，在中等至优异的产率下含有新构建的季碳原子中心。反应通过顺序羧化、ArPdX 物种对 C≡C 键的反式氧化钯化和导致带有四取代乙烯片段的苯并恶嗪-2-酮的还原消除过程进行。然后，苯并恶嗪-2-酮发生重排生成 3,3-二芳基 2,4-喹啉二酮。该方法的特点是一锅法同时形成四个键。
