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 -difluoroallylic bicyclo[1.1.1]pentanes visible light-induced defluorinat...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (35), p.5213-5216
Hauptverfasser: Zhu, Hui, Wu, Shengxing, Zhu, Bingbin, Li, Jiacheng, Lan, Deyou, Xu, Wenhao, Xu, Gongcheng, Zhu, Yu, Yu, Chuanming, Jiang, Xinpeng
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Sprache:eng
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Zusammenfassung: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 -difluoroallylic bicyclo[1.1.1]pentanes visible light-induced defluorinative -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 α-trifluoromethyl alkenes to form -difluoroallylic bicyclo[1.1.1]pentanes. Importantly, our methodology is characterized by mild reaction conditions, wide reactant scope, and suitable functional group tolerance.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00822c