Yichen Sun, Zhibin Hu, Jing Peng, Qixue Qin and Ning Jiao
{"title":"I2/DMSO催化体系对环丁烯酮Baeyer-Villiger氧化的替代方法","authors":"Yichen Sun, Zhibin Hu, Jing Peng, Qixue Qin and Ning Jiao","doi":"10.1039/D3GC01756G","DOIUrl":null,"url":null,"abstract":"<p >The Baeyer–Villiger oxidation represents a valuable reaction that enables the conversion of ketones into esters or lactones. Here, we present a novel and efficient approach utilizing I<small><sub>2</sub></small> as a catalyst for the oxidative rearrangement of cyclobutenones, resulting in the synthesis of furan-2(5<em>H</em>)-one. Notably, this method employs dimethyl sulfoxide (DMSO) as a greener oxidant and source of oxygen. The reaction proceeds smoothly with catalytic amounts of iodine, yielding lactones in good yields. Compared to conventional Baeyer–Villiger oxidation reactions that rely on peroxyl acids or hydrogen peroxide, the use of DMSO offers a safer and more versatile alternative.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":" 18","pages":" 7079-7083"},"PeriodicalIF":9.3000,"publicationDate":"2023-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I2/DMSO catalytic systems†\",\"authors\":\"Yichen Sun, Zhibin Hu, Jing Peng, Qixue Qin and Ning Jiao\",\"doi\":\"10.1039/D3GC01756G\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The Baeyer–Villiger oxidation represents a valuable reaction that enables the conversion of ketones into esters or lactones. Here, we present a novel and efficient approach utilizing I<small><sub>2</sub></small> as a catalyst for the oxidative rearrangement of cyclobutenones, resulting in the synthesis of furan-2(5<em>H</em>)-one. Notably, this method employs dimethyl sulfoxide (DMSO) as a greener oxidant and source of oxygen. The reaction proceeds smoothly with catalytic amounts of iodine, yielding lactones in good yields. Compared to conventional Baeyer–Villiger oxidation reactions that rely on peroxyl acids or hydrogen peroxide, the use of DMSO offers a safer and more versatile alternative.</p>\",\"PeriodicalId\":78,\"journal\":{\"name\":\"Green Chemistry\",\"volume\":\" 18\",\"pages\":\" 7079-7083\"},\"PeriodicalIF\":9.3000,\"publicationDate\":\"2023-08-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2023/gc/d3gc01756g\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2023/gc/d3gc01756g","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I2/DMSO catalytic systems†
The Baeyer–Villiger oxidation represents a valuable reaction that enables the conversion of ketones into esters or lactones. Here, we present a novel and efficient approach utilizing I2 as a catalyst for the oxidative rearrangement of cyclobutenones, resulting in the synthesis of furan-2(5H)-one. Notably, this method employs dimethyl sulfoxide (DMSO) as a greener oxidant and source of oxygen. The reaction proceeds smoothly with catalytic amounts of iodine, yielding lactones in good yields. Compared to conventional Baeyer–Villiger oxidation reactions that rely on peroxyl acids or hydrogen peroxide, the use of DMSO offers a safer and more versatile alternative.
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.