Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols
文献类型：期刊论文
| 作者 | Ma, Shuang-Shuang2,3; Sun, Rui2,3; Zhang, Zi-Heng1,2; Yu, Zheng-Kun4; Xu, Bao-Hua2,3,4 |
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2021-10-13 |
| 页码 | 10 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/d1qo01269j |
| 英文摘要 | The alkylation of nitroarenes with alkanols catalysed by a phosphinesulfonate chelated ruthenium complex [Ru-1] was developed. It exhibits very different reactivity and chemoselectivity depending on acidic-basic conditions. Under either neutral or acidic conditions, nitroarenes were converted to secondary and tertiary anilines, respectively, with secondary and primary alkanols. By contrast, the same catalyst promotes the N-monoalkylation of nitroarenes with primary alkanols under alkaline conditions, while both N-monoalkylation with secondary alkanols and N-dialkylation with primary alkanols are inhibited. Mechanistic studies demonstrated that the novel reactivity under alkaline-free conditions is attributed to the sulfonate ligand-assisted O-H activation of alkanols, thus enabling the reduction of nitroarenes and nucleophilic C-N coupling in a concerted approach. Furthermore, it follows the traditional two-step approach, taking the corresponding imines as the intermediates, under alkaline conditions. Based on such features, diverse secondary and tertiary anilines were obtained directly from nitroarenes using the same catalyst [Ru-1]. |
| WOS关键词 | REDUCTIVE N-ALKYLATION ; H BOND ACTIVATION ; NITRO-COMPOUNDS ; BORONIC ACIDS ; ELECTROPHILIC AMINATION ; COOPERATIVE CATALYSIS ; SECONDARY-AMINES ; BRONSTED ACID ; ALCOHOLS ; LIGANDS |
| 资助项目 | Excellent Young Scientists Fund[22022815] ; Innovation Academy for Green Manufacture, CAS[IAGM2020C13] ; Zhengzhou High Level Talent Certificate[20180200052] ; K. C. Wong Education Foundation[GJTD-2018-04] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000712551200001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 资助机构 | Excellent Young Scientists Fund ; Innovation Academy for Green Manufacture, CAS ; Zhengzhou High Level Talent Certificate ; K. C. Wong Education Foundation |
| 源URL | [http://ir.ipe.ac.cn/handle/122111/50830]  |
| 专题 | 中国科学院过程工程研究所 |
| 通讯作者 | Xu, Bao-Hua |
| 作者单位 | 1.Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China 2.Chinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China 3.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China 4.Chinese Acad Sci, Innovat Acad Green Manufacture, Beijing 100190, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ma, Shuang-Shuang,Sun, Rui,Zhang, Zi-Heng,et al. Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols[J]. ORGANIC CHEMISTRY FRONTIERS,2021:10. |
| APA | Ma, Shuang-Shuang,Sun, Rui,Zhang, Zi-Heng,Yu, Zheng-Kun,&Xu, Bao-Hua.(2021).Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols.ORGANIC CHEMISTRY FRONTIERS,10. |
| MLA | Ma, Shuang-Shuang,et al."Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols".ORGANIC CHEMISTRY FRONTIERS (2021):10. |
入库方式： OAI收割
来源：过程工程研究所
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