Facile access to the 2,2-difluoro-2,3-dihydrofuran skeleton without extra additives: DMF-promoted difluorocarbene formation of ClCF2CO2Na

A practical and facile difluorocarbene-triggered cycloaddition reaction of enaminones was developed, which delivered 2,2-difluoro-2,3-dihydrofurans with a broad substrate scope. Notably, the reaction proceeded smoothly without any extra additives. Readily available sodium chlorodifluoroacetate (ClCF...

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Veröffentlicht in:Organic & biomolecular chemistry 2022-10, Vol.20 (41), p.8037-8041
Hauptverfasser: Chen, Zunsheng, Xie, Xin, Chen, Weiming, Luo, Nianhua, Li, Xiaoning, Yu, Fuchao, Huang, Jiuzhong
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Sprache:eng
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Zusammenfassung:A practical and facile difluorocarbene-triggered cycloaddition reaction of enaminones was developed, which delivered 2,2-difluoro-2,3-dihydrofurans with a broad substrate scope. Notably, the reaction proceeded smoothly without any extra additives. Readily available sodium chlorodifluoroacetate (ClCF2CO2Na, SCDA) served as a difluorocarbene precursor in this transformation through DMF-promotion. Moreover, it is proved that the 2,2-difluoro-2,3-dihydrofuran derivatives exhibit potential antiproliferative activity against human tumour cells HeLa, MCF7 and HepG2.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01542k