Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement
2022-04
Source PublicationMOLECULES
EISSN1420-3049
Volume27Issue:8
Status已发表
DOI10.3390/molecules27082570
AbstractChiral 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.
Keywordball mill mechanochemistry solid-state reactions chiral vicinal diamine silica gel
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Indexed BySCI ; SCIE
Language英语
Funding ProjectAnalytical Instrumentation Center, SPST, ShanghaiTech University[SPST-AIC10112914]
WOS Research AreaBiochemistry & Molecular Biology ; Chemistry
WOS SubjectBiochemistry & Molecular Biology ; Chemistry, Multidisciplinary
WOS IDWOS:000786016300001
PublisherMDPI
Citation statistics
Document Type期刊论文
Identifierhttps://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 AuthorYan, 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 AffilicationSchool of Physical Science and Technology
Corresponding Author AffilicationSchool of Physical Science and Technology
First Signature AffilicationSchool 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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