Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control
文献类型：期刊论文
| 作者 | Xiang, Keyu2; Shou, Haowen1,2; Hu, Chenhui2; Su, Weike2; Yu, Jingbo2 |
| 刊名 | GREEN CHEMISTRY
 |
| 出版日期 | 2024-04-09 |
| 页码 | 10 |
| ISSN号 | 1463-9262 |
| DOI | 10.1039/d4gc01006j |
| 通讯作者 | Yu, Jingbo(yjb@zjut.edu.cn) |
| 英文摘要 | The oxidative Heck reaction is a well-known organic transformation. However, previous reactions have been limited by the need for sophisticated directing or auxiliary groups, reliance on bulk solvents, lack of catalyst recycling, and the formation of a mixture of isomeric products, thereby hindering its broader application. Herein, we present a novel approach utilizing the polymer-assisted grinding (POLAG) technique to facilitate the regioselective oxidative Heck coupling of aryl boronic acids with electronically unbiased olefins under solvent-free conditions. This catalytic reaction is facilitated by a ligand-free Pd(TFA)2 catalyst in conjunction with cyclodextrin (CD) serving as a POLAG additive and molecular oxygen as the green oxidant. Mechanistic studies have indicated that cyclodextrin not only stabilizes the palladium catalyst but also influences the reaction selectivity by imposing steric hindrance on the substrates. Recovery experiments and electron microscopy images demonstrate an effective recovery capability of Pd/CD, with the catalyst morphology largely preserved after five cycles. XPS experiments confirm the formation of a new palladium catalytic species during the ball-milling process. Remarkably, this reaction takes place at ambient temperature, obviating the need for additional stoichiometric amounts of hazardous oxidants and toxic solvents, aligning with environmentally friendly practices upon green metrics evaluation. A novel approach utilizing the polymer-assisted grinding (POLAG) technique to facilitate the regioselective oxidative Heck coupling of aryl boronic acids with electronically unbiased olefins under solvent-free conditions was presented. |
| WOS关键词 | HETEROGENEOUS LIGAND ; ORGANIC-SYNTHESIS ; MIXER MILL ; ACIDS ; OPPORTUNITIES ; OLEFINATION ; CATALYST ; WALKING |
| 资助项目 | Natural Science Foundation of Zhejiang Province[LY23B060005] ; Natural Science Foundation of Zhejiang Province[2021YFC2101000] ; National Key R&D Program of China[21978270] ; National Natural Science Foundation of China |
| WOS研究方向 | Chemistry ; Science & Technology - Other Topics |
| 语种 | 英语 |
| WOS记录号 | WOS:001204238200001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/310641]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Yu, Jingbo |
| 作者单位 | 1.Shanghai Inst Mat Med, Chinese Acad Sci, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gre, Lab Pharmaceut Engn Zhejiang Prov, Key Lab Green Pharmaceut Technol & Related Equipme, Hangzhou 310014, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xiang, Keyu,Shou, Haowen,Hu, Chenhui,et al. Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control[J]. GREEN CHEMISTRY,2024:10. |
| APA | Xiang, Keyu,Shou, Haowen,Hu, Chenhui,Su, Weike,&Yu, Jingbo.(2024).Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control.GREEN CHEMISTRY,10. |
| MLA | Xiang, Keyu,et al."Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control".GREEN CHEMISTRY (2024):10. |
入库方式： OAI收割
来源：上海药物研究所
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