Palladium‐Catalyzed Oxidative Cyclocarbonylation of Isoquinolones with CO via C−H/N−H Bond Cleavage: Easy Access to Isoindolo[2,1‐b]isoquinoline‐5,7‐dione Derivatives,Advanced Synthesis & Catalysis

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Palladium‐Catalyzed Oxidative Cyclocarbonylation of Isoquinolones with CO via C−H/N−H Bond Cleavage: Easy Access to Isoindolo[2,1‐b]isoquinoline‐5,7‐dione Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-05-11 , DOI: 10.1002/adsc.201800347
Shenghai Guo ₁ , Fang Wang ₁ , Lincong Sun ₁ , Xinying Zhang ₁ , Xuesen Fan ₁

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An efficient and practical synthesis of isoindolo[2,1‐b]isoquinoline‐5,7‐diones through Pd‐catalyzed C−H activation/carbonylative annulation of isoquinolones with CO (1 atm) is presented. Deuterium‐labeling experiments revealed that the aryl C(sp²)−H bond activation might be the rate‐determining step. More interestingly, the title compounds could also be prepared directly from the cascade reaction of N‐methoxy benzamides and internal alkynes, as the precursors of isoquinolones, under an atmospheric pressure of carbon monoxide through a Rh/Pd relay catalysis in a user‐friendly manner.

中文翻译：

钯通过CH / N-H键裂解与CO催化的异喹啉酮与CO的氧化环羰基化：容易获得Isoindolo [2,1-b] isoquinoline-5,7-dione衍生物

提出了一种通过Pd催化的CH活化/异喹啉酮与CO（1 atm）羰基环化反应有效合成异吲哚并[2,1 – b ]异喹啉-5,7-二酮的方法。氘标记实验表明，芳基C（sp ²）-H键的活化可能是决定速率的步骤。更有趣的是，标题化合物也可以直接由N-甲氧基苯甲酰胺和内部炔烃（作为异喹诺酮的前体）在一氧化碳的大气压下，通过Rh / Pd中继催化，以用户友好的方式级联反应制备。。

更新日期：2018-05-11

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