{"title":"Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines","authors":"Xiao-Ying Li, Ming-Yao Tang, Qian Tong, Danhua Ge, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu","doi":"10.1021/acs.orglett.5c00381","DOIUrl":null,"url":null,"abstract":"A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH<sub>2</sub>O)<sub>n</sub>, and (NH<sub>4</sub>)<sub>2</sub>CO<sub>3</sub> through the cleavage of five inert C(sp<sup>3</sup>)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (<i>E</i>)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this reaction features mild reaction conditions, good compatibility with various functional groups, excellent <i>E</i>-stereoselectivity, late-stage modification of complex molecules, scalability, and versatile synthetic transformations of the resulting heterocyclic compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00381","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, and (NH4)2CO3 through the cleavage of five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this reaction features mild reaction conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification of complex molecules, scalability, and versatile synthetic transformations of the resulting heterocyclic compounds.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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