期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 46, 页码 18475-18485出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07607
关键词
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资金
- NSFC [21702027, 21871043, 21773025]
- Young Scientific Research Foundation of Jilin Province [20180520228JH]
- Scientific Research Foundation of Education Department of Jilin Province [JJKH20180013KJ]
- Fundamental Research Funds for the Central Universities [2412017QD010, 2412019FZ017]
A diverse collection of copper-catalyzed intermolecular aminative difunctionalizations of unactivated alkenes with N-halodialkylamines as the terminal dialkylamino source is reported. A bidentate auxiliary tethered on the alkene substrates is crucial, which can promote the migratory insertion of nonactivated alkenes into the aminyl radical-metal complex and stabilize the resultant high-valent copper intermediate to allow for further transformations. By employing this strategy, the intermolecular aminohalogenation reactions and a three-component aminoazidation reaction of unactivated alkenes with dialkylamino source were successively achieved in a remarkable regio- and stereoselective manner. These reactions were performed under neutral conditions and maintained excellent functional group tolerance toward a wide range of N-halodialkylamines and unactivated alkenes. Further mechanistic studies and DFT calculations supported a concerted migratory insertion of the C-C double bond into the aminyl radical-metal complex to form a Cu(III) intermediate.
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