Iron-catalysed reductive coupling for the synthesis of polyfluorinated compounds

Herein we reported the use of Earth-abundant iron as the catalytic metal in the presence of Mn to induce difluorobromoacetates to form carbon radicals, which reacted with trifluoromethyl olefins followed by -F elimination to generate the corresponding gem -difluoroolefins. The cross-electrophile cou...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-12, Vol.58 (1), p.13915-13918
Hauptverfasser: Guan, Yu-Qiu, Wang, Tian-Zhang, Qiao, Jia-Fan, Chen, Zhangpei, Bai, Zhushuang, Liang, Yu-Feng
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Sprache:eng
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Zusammenfassung:Herein we reported the use of Earth-abundant iron as the catalytic metal in the presence of Mn to induce difluorobromoacetates to form carbon radicals, which reacted with trifluoromethyl olefins followed by -F elimination to generate the corresponding gem -difluoroolefins. The cross-electrophile coupling displayed excellent functional group tolerance and broad substrate scope under mild reductive conditions, affording a large number of polyfluorinated compounds, which could be further transformed to other valuable molecules. Iron-catalysed reductive cross-coupling of difluorobromo acetic acid derivatives with trifluoromethyl olefins to afford polyfluorinated molecules, containing a difluorenyl and difluoroalkyl group, with a broad substrate scope.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc06022a