ShanghaiTech University Knowledge Management System
| Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement | |
| 2022-04 | |
| Source Publication | MOLECULES
 |
| EISSN | 1420-3049 |
| Volume | 27Issue:8 |
| Status | 已发表 |
| DOI | 10.3390/molecules27082570 |
| Abstract | Chiral vicinal diamines, a unique class of optically-active building blocks, play a crucial role in material design, pharmaceutical, and catalysis. Traditionally, their syntheses are all solvent-based approaches, which make organic solvent an indispensable part of their production. As part of our program aiming to develop chemical processes with reduced carbon footprints, we recently reported a highly practical and environmentally-friendly synthetic route to chiral vicinal diamines by solvent-free mechanochemical diaza-Cope rearrangement. We herein showed that a new protocol by co-milling with common laboratory solid additives, such as silica gel, can significantly enhance the efficiency of the reaction, compared to reactions in the absence of additives. One possible explanation is the Lewis acidic nature of additives that accelerates a key Schiff base formation step. Reaction monitoring experiments tracing all the reaction species, including reactants, intermediates, and product, suggested that the reaction profile is distinctly different from ball-milling reactions without additives. Collectively, this work demonstrated that additive effect is a powerful tool to manipulate a reaction pathway in mechanochemical diazo-Cope rearrangement pathway, and this is expected to find broad interest in organic synthesis using mechanical force as an energy input. |
| Keyword | ball mill mechanochemistry solid-state reactions chiral vicinal diamine silica gel |
| URL | 查看原文 |
| Indexed By | SCI ; SCIE |
| Language | 英语 |
| Funding Project | Analytical Instrumentation Center, SPST, ShanghaiTech University[SPST-AIC10112914] |
| WOS Research Area | Biochemistry & Molecular Biology ; Chemistry |
| WOS Subject | Biochemistry & Molecular Biology ; Chemistry, Multidisciplinary |
| WOS ID | WOS:000786016300001 |
| Publisher | MDPI |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/176036 |
| Collection | 物质科学与技术学院_博士生 物质科学与技术学院_硕士生 物质科学与技术学院_PI研究组_甄家劲组 |
| Corresponding Author | Yan, Kaking |
| Affiliation | 1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Chinese Acad Sci, Shanghai Adv Res Inst, Shanghai 201203, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| First Author Affilication | School of Physical Science and Technology |
| Corresponding Author Affilication | School of Physical Science and Technology |
| First Signature Affilication | School of Physical Science and Technology |
| Recommended Citation GB/T 7714 | Cheng, Tingting,Ma, Wenxian,Luo, Hao,et al. Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement[J]. MOLECULES,2022,27(8). |
| APA | Cheng, Tingting,Ma, Wenxian,Luo, Hao,Ye, Yangzhi,&Yan, Kaking.(2022).Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement.MOLECULES,27(8). |
| MLA | Cheng, Tingting,et al."Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement".MOLECULES 27.8(2022). |
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