Jia-Min Lu, Yihui Mao, Qihang Guo, Chengcheng Zhong, Xian-Ge Gao, Qun Fang and Zhan Lu
{"title":"Metal-free stereoselective intramolecular oxyamination of alkynes using a robotic and rapid photocatalytic synthesis and screening system†","authors":"Jia-Min Lu, Yihui Mao, Qihang Guo, Chengcheng Zhong, Xian-Ge Gao, Qun Fang and Zhan Lu","doi":"10.1039/D4GC05100A","DOIUrl":null,"url":null,"abstract":"<p >A unique metal-free and 100% atom-economical method for intramolecular oxyamination of alkynes with high stereoselectivity <em>via</em> 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 <em>Z</em> 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.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":" 3","pages":" 560-565"},"PeriodicalIF":9.3000,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/gc/d4gc05100a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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.
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.