Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate

Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate

A Cu-catalyzed regioselective bromodifluoroacetylation of alkenes, using ethyl bromodifluoroacetate (BrCF2CO2Et) as a difluoroacetylating reagent, has been disclosed. The reaction proceeds under mild conditions, and possible byproducts generated from hydrodifluoroacetylation and/or direct alkenyl C–...

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Veröffentlicht in:Journal of organic chemistry 2018-09, Vol.83 (17), p.10445-10452
Hauptverfasser: Li, Dengke, Mao, Tingting, Huang, Jinbo, Zhu, Qiang
Format: Artikel
Sprache:eng
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Zusammenfassung:A Cu-catalyzed regioselective bromodifluoroacetylation of alkenes, using ethyl bromodifluoroacetate (BrCF2CO2Et) as a difluoroacetylating reagent, has been disclosed. The reaction proceeds under mild conditions, and possible byproducts generated from hydrodifluoroacetylation and/or direct alkenyl C–H difluoroacetylation are not observed. Mechanistic studies confirm that the atom transfer radical addition (ATRA) process is involved in this alkene difunctionalization reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01434