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Lewis acid catalyzed intermolecular olefin hydroamination: Scope, limitation, and mechanism
Cheng, Xiaojuan1; Xia, Yuanzhi1,2; Wei, Hua1; Xu, Bin2; Zhang, Chongguang1; Li, Yahong1,2,3; Qian, Guimin2; Zhang, Xiaohua1; Li, Kai1; Li, Wu2
2008-04-01
Source PublicationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Issue11Pages:1929-1936
SubtypeArticle
AbstractIntermolecular olefin hydroamination was studied by various Lewis acids. The results of ZrCl(4), FeCl(3), BiCl(3), and AlCl(3) catalyzed reactions of norbornene with aromatic amines were compared, and BiCl(3) was found to be the most effective catalyst to give high yields for various amines, whereas ZrCl(4) could promote the reactions at relatively low temperatures. The FeCl(3) catalyzed reactions were the most chemoselective and excellent yields could be achieved for certain amines by using AlCl(3). A carbocation mechanism was proposed, and the controllable syntheses of allylamine and tetrahydroquinoline from isoprene and 2,5-dichloroaniline were achieved by application of this mechanism. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
KeywordHydroamination Lewis Acids Amines Catalysis Mechanisms
WOS HeadingsScience & Technology ; Physical Sciences
WOS KeywordINTRAMOLECULAR HYDROAMINATION ; ASYMMETRIC HYDROAMINATION ; BRONSTED ACID ; STEREOSELECTIVE-SYNTHESIS ; HYDROARYLATION REACTIONS ; VINYLSILANES BEARING ; UNACTIVATED OLEFINS ; CARBOXYLIC-ACIDS ; IONIC SOLVENTS ; AMINO GROUP
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000255144100010
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Cited Times:44[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.isl.ac.cn/handle/363002/5865
Collection青海盐湖研究所知识仓储
盐湖资源综合利用工程技术中心
Affiliation1.Suzhou Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem & Chem Engn, Suzhou 215123, Peoples R China
2.Chinese Acad Sci, Qinghai Inst Salt Lakes, Xining 810008, Peoples R China
3.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Cheng, Xiaojuan,Xia, Yuanzhi,Wei, Hua,et al. Lewis acid catalyzed intermolecular olefin hydroamination: Scope, limitation, and mechanism[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2008(11):1929-1936.
APA Cheng, Xiaojuan.,Xia, Yuanzhi.,Wei, Hua.,Xu, Bin.,Zhang, Chongguang.,...&Li, Wu.(2008).Lewis acid catalyzed intermolecular olefin hydroamination: Scope, limitation, and mechanism.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11),1929-1936.
MLA Cheng, Xiaojuan,et al."Lewis acid catalyzed intermolecular olefin hydroamination: Scope, limitation, and mechanism".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .11(2008):1929-1936.
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