| 题名 | Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles |
| 作者 | |
| 通讯作者 | Ding, Wei-Yi; Zhong, Guofu; Tan, Bin |
| 发表日期 | 2021-10-01
|
| DOI | |
| 发表期刊 | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
|
| 卷号 | 60页码:24888-24893 |
| 摘要 | Described herein is an imidazole ring formation strategy for the synthesis of axially chiral N-arylbenzimidazoles by means of chiral phosphoric acid catalysis. Two sets of conditions were developed to transform two classes of 2-naphthylamine derivatives into structurally diverse N-arylbenzimidazole atropisomers with excellent chemo- and regioselectivity as well as high levels of enantiocontrol. It is worth reflecting on the unique roles played by the nitroso group in this domino reaction. It functions as a linchpin by first offering an electrophilic site (N) for the initial C-N bond formation while the resulting amine performs the nucleophilic addition to form the second C-N bond. Additionally, it could facilitate the final oxidative aromatization as an oxidant. The atropisomeric products could be conveniently elaborated to a series of axially chiral derivatives, enabling the exploitation of N-arylbenzimidazoles for their potential utilities in asymmetric catalysis. |
| 关键词 | |
| 相关链接 | [来源记录] |
| 收录类别 | |
| 语种 | 英语
|
| 重要成果 | NI论文
|
| 学校署名 | 第一
; 通讯
|
| 资助项目 | National Natural Science Foundation of China[21672048,21825105]
; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
; Guangdong Innovative Program[2019BT02Y335]
; Shenzhen Special Funds[JCYJ20180302174106405]
; Shenzhen Nobel Prize Scientists Laboratory Project[C17213101]
; SUSTech Special Fund for the Construction of High-Level Universities[G02216302]
|
| WOS研究方向 | Chemistry
|
| WOS类目 | Chemistry, Multidisciplinary
|
| WOS记录号 | WOS:000708106400001
|
| 出版者 | |
| EI入藏号 | 20214211035033
|
| EI主题词 | Addition reactions
; Catalysis
; Reaction kinetics
|
| EI分类号 | Chemical Reactions:802.2
; Inorganic Compounds:804.2
|
| ESI学科分类 | CHEMISTRY
|
| 来源库 | Web of Science
|
| 引用统计 |
被引频次[WOS]：49
|
| 成果类型 | 期刊论文 |
| 条目标识符 | http://sustech.caswiz.com/handle/2SGJ60CL/254168 |
| 专题 | 深圳格拉布斯研究院 理学院_化学系 |
| 作者单位 | 1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China 2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China 3.Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Peoples R China |
| 第一作者单位 | 深圳格拉布斯研究院; 化学系 |
| 通讯作者单位 | 深圳格拉布斯研究院; 化学系 |
| 第一作者的第一单位 | 深圳格拉布斯研究院 |
| 推荐引用方式 GB/T 7714 |
An, Qian-Jin,Xia, Wang,Ding, Wei-Yi,et al. Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60:24888-24893.
|
| APA |
An, Qian-Jin.,Xia, Wang.,Ding, Wei-Yi.,Liu, Huan-Huan.,Xiang, Shao-Hua.,...&Tan, Bin.(2021).Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60,24888-24893.
|
| MLA |
An, Qian-Jin,et al."Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60(2021):24888-24893.
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| 条目包含的文件 | ||||||
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| Angew Chem Int Ed - （2029KB） | -- | -- | 限制开放 | -- | ||
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