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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
发表期刊TETRAHEDRON
ISSN0040-4020
卷号74期号:18页码:2230-2238
摘要A 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.
关键词Nitrone Beta-c(Sp(3))-h Functionalization Aldol Condensation Alpha Deoxygenation Beta-unsaturated Imine
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
DOI10.1016/j.tet.2018.03.038
收录类别SCI
语种英语
关键词[WOS]AMINE-N-OXIDES ; LEWIS-BASE ACTIVATION ; C-H FUNCTIONALIZATION ; BETA-CONDENSATION REACTIONS ; SILYL KETENE ACETALS ; CYCLIC AMINES ; FACILE DEOXYGENATION ; ALIPHATIC-AMINES ; O BOND ; ALDEHYDES
WOS研究方向Chemistry
WOS类目Chemistry, Organic
项目资助者National Natural Science Foundation of China(U1662133 ; Instrument Developing Project of the Chinese Academy of Sciences(YZ201521) ; CAS 100-Talent Program ; 21476240)
WOS记录号WOS:000430899300006
引用统计
文献类型期刊论文
条目标识符http://ir.ipe.ac.cn/handle/122111/24429
专题多相复杂系统国家重点实验室
作者单位1.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
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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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