Radical-Polar Crossover Enabled Triple Cleavage of CF2Br2: A Multicomponent Tandem Cyclization to 3‑Fluoropyrazoles

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein is a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as a novel C1F1 synthon. Mechanistic expe...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 32; pp. 6062 - 6066
Main Authors Zuo, Wanqing, Zuo, Lingling, Geng, Xiao, Li, Zhifang, Wang, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein is a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as a novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation of the reactive intermediate gem-difluorovinylimine ion is the key to this transformation. This protocol unlocks the novel reactivity of CF2Br2 and adds significant synthetic values to fluorine chemistry.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02305