{"title":"Synthesis of fluoroalkenes via Julia and Julia-Kocienski olefination reactions","authors":"Qinyu Luo, Xiu Wang, Jinbo Hu","doi":"10.1016/j.tet.2022.132694","DOIUrl":null,"url":null,"abstract":"<div><p><span><span><span>The introduction of one or two fluorine atoms into a carbon-carbon double bond often brings about profound changes of physical, chemical and/or biological properties of the target molecule. Fluorinated </span>alkenes are a class of important compounds and widely used in medicinal </span>chemistry and materials science. Julia and Julia-Kocienski reactions could be used in the synthesis of fluorinated alkenes by employing α-fluorinated </span>sulfones. In this review, the synthesis of fluorinated alkenes through Julia and Julia-Kocienski reactions are summarized, and the contents are categorized by target molecules and sulfone reagents. The difference between the reaction conditions for monofluoromethyl sulfones and difluoromethyl sulfones reflects the unique effect of fluorine substituents.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"113 ","pages":"Article 132694"},"PeriodicalIF":2.1000,"publicationDate":"2022-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402022000801","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 3
Abstract
The introduction of one or two fluorine atoms into a carbon-carbon double bond often brings about profound changes of physical, chemical and/or biological properties of the target molecule. Fluorinated alkenes are a class of important compounds and widely used in medicinal chemistry and materials science. Julia and Julia-Kocienski reactions could be used in the synthesis of fluorinated alkenes by employing α-fluorinated sulfones. In this review, the synthesis of fluorinated alkenes through Julia and Julia-Kocienski reactions are summarized, and the contents are categorized by target molecules and sulfone reagents. The difference between the reaction conditions for monofluoromethyl sulfones and difluoromethyl sulfones reflects the unique effect of fluorine substituents.
期刊介绍：
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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