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SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones to alpha,beta-unsaturated imines and aromatic heterocycles
Zhu, De-Ping1,2; Xu, Bao-Hua1,2; Du, Yi-Ran1,2; Zhang, Suo-Jiang1,2
2018-05-03
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume74Issue:18Pages:2230-2238
AbstractA novel method of SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones with aldehydes/ketones to alpha,beta-unsaturated imines was developed. The synthesis of 4-unsaturated imines mainly invovles deoxygenation and aldol condensation, each proceeding under a cooperation effect between Lewis acid and Lewis base. In addition, both the acidity and hydrolytic stability of the weak SiCl4 were supposed to be enhanced by coordination with phosphine oxide (R = Et) or phosphoric triamide (R = NMe2) that originated from deoxygenation of nitrones by PR3. In the case of 6-membered nitrone, a [1,3]-hydride shift within the resulted alpha,beta-unsaturated imines renders the aromatization leading to 3,5-dialkylpyridines. (C) 2018 Elsevier Ltd. All rights reserved.
KeywordNitrone Beta-c(Sp(3))-h Functionalization Aldol Condensation Alpha Deoxygenation Beta-unsaturated Imine
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1016/j.tet.2018.03.038
Indexed BySCI
Language英语
WOS KeywordAMINE-N-OXIDES ; LEWIS-BASE ACTIVATION ; C-H FUNCTIONALIZATION ; BETA-CONDENSATION REACTIONS ; SILYL KETENE ACETALS ; CYCLIC AMINES ; FACILE DEOXYGENATION ; ALIPHATIC-AMINES ; O BOND ; ALDEHYDES
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationNational Natural Science Foundation of China(U1662133 ; Instrument Developing Project of the Chinese Academy of Sciences(YZ201521) ; CAS 100-Talent Program ; 21476240)
WOS IDWOS:000430899300006
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/24429
Collection多相复杂系统国家重点实验室
Affiliation1.Chinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, Inst Proc Engn, Key Lab Green Proc & Engn,State Key Lab Multiphas, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhu, De-Ping,Xu, Bao-Hua,Du, Yi-Ran,et al. SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones to alpha,beta-unsaturated imines and aromatic heterocycles[J]. TETRAHEDRON,2018,74(18):2230-2238.
APA Zhu, De-Ping,Xu, Bao-Hua,Du, Yi-Ran,&Zhang, Suo-Jiang.(2018).SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones to alpha,beta-unsaturated imines and aromatic heterocycles.TETRAHEDRON,74(18),2230-2238.
MLA Zhu, De-Ping,et al."SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones to alpha,beta-unsaturated imines and aromatic heterocycles".TETRAHEDRON 74.18(2018):2230-2238.
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