Co-Catalyzed atom transfer radical addition of bromodifluoroacetamides, expanding the scope of radical difluoroalkylation

The atom transfer radical addition (ATRA) of bromodifluoroacetamides to arylalkynes and terminal alkenes was conducted using von Wangelin's Co catalyst system (CoBr 2 /1,2-bis(diphenylphosphino)benzene/Zn) in acetone/H 2 O at 30 °C to afford the corresponding functionalized difluoroacetamides i...

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Veröffentlicht in:Organic & biomolecular chemistry 2022-04, Vol.2 (14), p.2867-2872
Hauptverfasser: Yamamoto, Yoshihiko, Suzuki, Harufumi, Kuroyanagi, Eisuke, Yamada, Keiji, Yasui, Takeshi
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Sprache:eng
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Zusammenfassung:The atom transfer radical addition (ATRA) of bromodifluoroacetamides to arylalkynes and terminal alkenes was conducted using von Wangelin's Co catalyst system (CoBr 2 /1,2-bis(diphenylphosphino)benzene/Zn) in acetone/H 2 O at 30 °C to afford the corresponding functionalized difluoroacetamides in 33-89% yields. Moreover, the Co catalyst was successfully applied to the tandem addition/cyclization of 1,6-diene and -enyne substrates and intramolecular ATRA of N -allyl and N -propargyl bromodifluoroacetamides, significantly expanding the scope of radical difluoroalkylation. The Co-catalyzed atom transfer radical addition (ATRA) of bromodifluoroacetamides to arylalkynes and alkenes afforded functionalized difluoroacetamides, expanding the scope of transition-metal-catalyzed ATRA.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00437b