Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement

doi:10.3390/molecules27082570

	Manipulating Reaction Energy Coordinate Landscape of Mechanochemical Diaza-Cope Rearrangement
	Cheng, Tingting1 ; Ma, Wenxian1,2,3 ; Luo, Hao1 ; Ye, Yangzhi1 ; Yan, Kaking1
	2022-04
发表期刊	MOLECULES
EISSN	1420-3049
卷号	27 期号:8
发表状态	已发表
DOI	10.3390/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
URL	查看原文
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
推荐引用方式 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).