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Scope and Mechanism of Allylic C-H Amination of Terminal Alkenes by the Palladium/PhI(OPiv)(2) Catalyst System: Insights into the Effect of Naphthoquinone
Alternative Title对钯/碘苯季戊酸催化体系下末端烯烃烯丙位碳氢键胺化反应范围和机理研究: 对萘醌作用的细节研究
Yin GY(阴国印); Wu YC(吴奕晨); Liu GS(刘国生)
2010
Source PublicationJ. Am. Chem. Soc.
ISSN0002-7863
Volume132Issue:34Pages:11978-11987
AbstractPalladium-catalyzed oxidative amination of unactivated alkyl olefins has been developed to produce linear (E)-allylimides with high regioselectivity. This highly efficient transformation of alkenes has been achieved by enhancing the reoxidation of palladium with the strong oxidant PhI(OPiv)(2). The present work also provides the first systematic analysis of the mechanism of the allylic C-H oxidative amination. It has been found that naphthoquinone (NQ) plays a vital role in promoting olefin coordination to the palladium catalyst: in the absence of NQ, the turnover-limiting step is olefin coordination to palladium catalyst; in the presence of NQ, the reaction involves a rapid equilibration to give a nitrogen-coordinated olefin-Pd(NQ) complex that undergoes turnover-limiting allylic C-H bond activation to generate a pi-allyl-Pd intermediate. This work provides valuable insights for further studies on the functionalization of unactivated olefins.
Subject Area金属有机化学
Department中国科学院上海有机化学研究所
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Indexed BySCI
Language英语
WOS IDWOS:000281296700045
Citation statistics
Cited Times:142[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/27877
Collection金属有机化学国家重点实验室
Corresponding AuthorLiu GS(刘国生)
Recommended Citation
GB/T 7714
Yin GY,Wu YC,Liu GS. Scope and Mechanism of Allylic C-H Amination of Terminal Alkenes by the Palladium/PhI(OPiv)(2) Catalyst System: Insights into the Effect of Naphthoquinone[J]. J. Am. Chem. Soc.,2010,132(34):11978-11987.
APA 阴国印,吴奕晨,&刘国生.(2010).Scope and Mechanism of Allylic C-H Amination of Terminal Alkenes by the Palladium/PhI(OPiv)(2) Catalyst System: Insights into the Effect of Naphthoquinone.J. Am. Chem. Soc.,132(34),11978-11987.
MLA 阴国印,et al."Scope and Mechanism of Allylic C-H Amination of Terminal Alkenes by the Palladium/PhI(OPiv)(2) Catalyst System: Insights into the Effect of Naphthoquinone".J. Am. Chem. Soc. 132.34(2010):11978-11987.
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