Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement
2022-04
发表期刊MOLECULES
EISSN1420-3049
卷号27期号:8
发表状态已发表
DOI10.3390/molecules27082570
摘要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.
关键词ball mill mechanochemistry solid-state reactions chiral vicinal diamine silica gel
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收录类别SCI ; SCIE
语种英语
资助项目Analytical Instrumentation Center, SPST, ShanghaiTech University[SPST-AIC10112914]
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
WOS类目Biochemistry & Molecular Biology ; Chemistry, Multidisciplinary
WOS记录号WOS:000786016300001
出版者MDPI
引用统计
文献类型期刊论文
条目标识符https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/176036
专题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
通讯作者Yan, Kaking
作者单位
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
第一作者单位物质科学与技术学院
通讯作者单位物质科学与技术学院
第一作者的第一单位物质科学与技术学院
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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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