Visible light-induced gem-difluoroallylation of [1.1.1]propellane to access gem-difluoroallylic bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentanes (BCPs) represent an important compound class often used as linear spacer units to enhance pharmacokinetic profiles in modern drug design. Herein, we report a cascade multicomponent reaction to synthesize gem-difluoroallylic bicyclo[1.1.1]pentanes via visible light-induced defl...

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Published inChemical communications (Cambridge, England) Vol. 59; no. 35; pp. 5213 - 5216
Main Authors Zhu, Hui, Wu, Shengxing, Zhu, Bingbin, Li, Jiacheng, Lan, Deyou, Xu, Wenhao, Xu, Gongcheng, Zhu, Yu, Yu, Chuanming, Jiang, Xinpeng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 27.04.2023
Royal Society of Chemistry
Subjects
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Functional groups
Pentanes
Physical Sciences
Science & Technology
CHEMISTRY
ALKENES
FLUORINE
DESIGN
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Summary:Bicyclo[1.1.1]pentanes (BCPs) represent an important compound class often used as linear spacer units to enhance pharmacokinetic profiles in modern drug design. Herein, we report a cascade multicomponent reaction to synthesize gem-difluoroallylic bicyclo[1.1.1]pentanes via visible light-induced defluorinative gem-difluoroallylation of [1.1.1]propellane. In this methodology, sulfonyl radicals generated from sodium arylsulfinates added to [1.1.1]propellane to form BCP radicals were then trapped by a-trifluoromethyl alkenes to form gem-difluoroallylic bicyclo[1.1.1]pentanes. Importantly, our methodology is characterized by mild reaction conditions, wide reactant scope, and suitable functional group tolerance.
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ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00822c