Metal-free stereoselective intramolecular oxyamination of alkynes using a robotic and rapid photocatalytic synthesis and screening system†

IF 9.3 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Green Chemistry Pub Date : 2024-12-17 DOI:10.1039/D4GC05100A
Jia-Min Lu, Yihui Mao, Qihang Guo, Chengcheng Zhong, Xian-Ge Gao, Qun Fang and Zhan Lu
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引用次数: 0

Abstract

A unique metal-free and 100% atom-economical method for intramolecular oxyamination of alkynes with high stereoselectivity via visible light photocatalysis is developed. Utilizing a robotic and rapid photocatalytic synthesis and screening system capable of anhydrous and oxygen-free flow synthesis, the standard reaction conditions were extensively investigated and optimized with reduced sample consumption, and an inexpensive and efficient organic photosensitizer was rapidly and successfully found. Starting from inexpensive, widely and readily available propargyl alcohol feedstock materials, single Z configuration 2-aminoprop-1-ene-1,3-diol derivatives could be obtained with good functional group compatibility and broad substrate scope. A possible mechanism involving a nitrogen radical process and nucleophilic attack was proposed based on the radical inhibition experiment and the cross-over experiment.

Abstract Image

使用机器人和快速光催化合成和筛选系统的无金属立体选择性炔的分子内氧化胺化
提出了一种独特的无金属、100%原子经济的可见光催化高立体选择性炔烃分子内氧化胺化反应方法。利用无水无氧流动合成的机器人快速光催化合成筛选系统,对标准反应条件进行了广泛的研究和优化,减少了样品消耗,快速成功地找到了一种廉价高效的有机光敏剂。从廉价、广泛、易得的丙炔醇原料出发,可以得到具有良好官能团相容性和广泛底物范围的单Z构型2-氨基丙烯-1,3-二醇衍生物。基于自由基抑制实验和交叉实验,提出了氮自由基过程和亲核攻击的可能机理。
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来源期刊
Green Chemistry
Green Chemistry 化学-化学综合
CiteScore
16.10
自引率
7.10%
发文量
677
审稿时长
1.4 months
期刊介绍: Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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