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
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes Alkenes - chemistry Benzene Catalysis Catalysts Cyclization Radicals Substrates
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creator	Yamamoto, Yoshihiko Suzuki, Harufumi Kuroyanagi, Eisuke Yamada, Keiji Yasui, Takeshi
description	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.
doi_str_mv	10.1039/d2ob00437b
format	Article
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subjects	Alkenes Alkenes - chemistry Benzene Catalysis Catalysts Cyclization Radicals Substrates
title	Co-Catalyzed atom transfer radical addition of bromodifluoroacetamides, expanding the scope of radical difluoroalkylation
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