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Palladium-Catalyzed Tandem Carbonylative Aza-Wacker-Type Cyclization of Nucleophile Tethered Alkene to Access Fused N-Heterocycles

查看全文 作　　者：Lijun [1,2]Shi;Mingshan [1]Wen;Fuwei [1]Li 高影响力作者 机构地区：[1]State Key Laboratory for Oxo Synthesis and Selective Oxidation,Suzhou Research Institute of LICP,Lanzhou Institute of Chemical Physics,Chinese Academy of Sciences,Lanzhou,Gansu,730000 China;[2]University of the Chinese Academy of Sciences,Beijing,100049 China高影响力机构 出　　处：《Chinese Journal of Chemistry》索引2021年第39卷第2期,共6页高影响力期刊 基　　金：This work was funded by the National Key R&D Program of China(No.2018YFB1501600);the Natural Science Foundation of China(Nos.21773271 and 21972151);the Light of West China of Chinese Academy of Sciences(CAS);the Key Research Program of Frontier Sciences of CAS(QYZDJSSW-SLH051). 摘　　要：Although tandem reactions offer rapid access to structurally complex molecules in one-pot reaction,the selectivity issue needs to be addressed particularly when incompatible step reactions are involved.Herein,we report the selective synthesis of fused N-heterocycles from nucleophile-tethered alkenylamide and carbon monoxide via palladium(Pd)-catalyzed tandem carbonylative aza-Wacker-type cyclization.The electron-deficient nature of amide N—H and the intramolecular coordination of Pd with alkene accelerate the aminopalladation and effectively prevent the side oxidative carbonylation of diamine moiety to form urea.It is also found that the reported acyl Pd chloride intermediate may not be involved in this tandem cyclization.This work not only provides an efficient synthetic route to fused 1,4-diazepanones and 1,4-diazepanes but also inspires further development of tandem reactions for the diverse synthesis of heterocycles. 关 键 词：Palladium CARBONYLATION HETEROCYCLES ALKENES Tandem reaction
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