钯催化连续亚胺/羰基化构建异喹啉酮四环化合物

Palladium-catalyzed cascade imidoylation/carbonylation to construct isoquinolinone tetracyclic compounds

以1,3-双(2-碘代芳基)丙烷-2-胺类化合物作为底物,通过钯催化的异腈和一氧化碳的连续插入反应,构建异喹啉酮类骨架。经研究发现,与异腈互为等电子体的一氧化碳虽然在反应中过量的存在,但是异腈仍然优先迁移插入芳基Pd(Ⅱ)中间体,随后再进行一氧化碳的插入,最后还原消除得到相应的异喹啉酮类四环化合物。该反应条件温和,产率高达85%,产物经^(1)H NMR,^(13)NMR,高分辨质谱鉴定正确。

Using 1,3-bis(2-iodoaryl)propane-2-amines as substrates,a palladium-catalyzed sequential insertion of isocyanide and carbon monoxide to construct isoquinolinone skeletons has been developed.Compared with isoelectronic isocyanide counterparts,the migratory insertion of isocyanide to Ar-Pd(Ⅱ)is still prefer to carbon monoxide although carbon monoxide exists in large excess in the reaction.Followed by carbon monoxide insertion and finally reductive elimination,the corresponding isoquinolinone tetracyclic compounds were obtained.The reaction conditions were mild and the yields are up to 85%.The product was correctly identified by ^(1)H NMR,^(13) NMR and high-resolution mass spectrometry.