SiCl4-catalyzed/PR3-mediated beta-C(sp(3))-H functionalization of nitrones to alpha,beta-unsaturated imines and aromatic heterocycles
文献类型：期刊论文
| 作者 | Zhu, De-Ping1,2; Xu, Bao-Hua1,2; Du, Yi-Ran1,2; Zhang, Suo-Jiang1,2 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2018-05-03 |
| 卷号 | 74期号:18页码:2230-2238 |
| 关键词 | Nitrone Beta-c(Sp(3))-h Functionalization Aldol Condensation Alpha Deoxygenation Beta-unsaturated Imine |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2018.03.038 |
| 文献子类 | Article |
| 英文摘要 | 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. |
| WOS关键词 | 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 |
| 语种 | 英语 |
| WOS记录号 | WOS:000430899300006 |
| 资助机构 | National Natural Science Foundation of China(U1662133 ; Instrument Developing Project of the Chinese Academy of Sciences(YZ201521) ; CAS 100-Talent Program ; 21476240) |
| 源URL | [http://ir.ipe.ac.cn/handle/122111/24429]  |
| 专题 | 过程工程研究所_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 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：过程工程研究所
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