Palladium-Catalyzed Tandem Carbonylative Aza-Wacker-Type Cyclization of Nucleophile Tethered Alkene to Access Fused N-Heterocycles | |
Shi Lijun1,2; Wen Mingshan2; Li Fuwei2 | |
刊名 | Chinese Journal of Chemistry |
2021-09-27 | |
卷号 | 39期号:2页码:317-322 |
关键词 | Palladium Tandem reaction Carbonylation Heterocycles Alkenes |
DOI | 10.1002/cjoc.202000491 |
英文摘要 | 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. |
语种 | 英语 |
WOS记录号 | WOS:000603404000001 |
内容类型 | 期刊论文 |
源URL | [http://ir.licp.cn/handle/362003/27686] |
专题 | 兰州化学物理研究所_OSSO国家重点实验室 兰州化学物理研究所_苏州研究院 |
通讯作者 | Li Fuwei |
作者单位 | 1.University of the Chinese Academy of Sciences, Beijing 100049, China 2.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 |
推荐引用方式 GB/T 7714 | Shi Lijun,Wen Mingshan,Li Fuwei. Palladium-Catalyzed Tandem Carbonylative Aza-Wacker-Type Cyclization of Nucleophile Tethered Alkene to Access Fused N-Heterocycles[J]. Chinese Journal of Chemistry,2021,39(2):317-322. |
APA | Shi Lijun,Wen Mingshan,&Li Fuwei.(2021).Palladium-Catalyzed Tandem Carbonylative Aza-Wacker-Type Cyclization of Nucleophile Tethered Alkene to Access Fused N-Heterocycles.Chinese Journal of Chemistry,39(2),317-322. |
MLA | Shi Lijun,et al."Palladium-Catalyzed Tandem Carbonylative Aza-Wacker-Type Cyclization of Nucleophile Tethered Alkene to Access Fused N-Heterocycles".Chinese Journal of Chemistry 39.2(2021):317-322. |
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