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

CORC > 上海有机化学研究所 > 中国科学院上海有机化学研究所 > 金属有机化学国家重点实验室

	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
	Yin GY(阴国印) ; Wu YC(吴奕晨) ; Liu GS(刘国生)
刊名	J. Am. Chem. Soc.
	2010
卷号	132 期号:34 页码:11978-11987
ISSN号	0002-7863
其他题名	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
通讯作者	刘国生
英文摘要	Palladium-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.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/ja1030936
语种	英语
WOS记录号	WOS:000281296700045
公开日期	2013-08-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/27877]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 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.