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

Org Biomol Chem

Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

Published: April 2022

The atom transfer radical addition (ATRA) of bromodifluoroacetamides to arylalkynes and terminal alkenes was conducted using von Wangelin's Co catalyst system (CoBr/1,2-bis(diphenylphosphino)benzene/Zn) in acetone/HO 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 -allyl and -propargyl bromodifluoroacetamides, significantly expanding the scope of radical difluoroalkylation.

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Source
http://dx.doi.org/10.1039/d2ob00437bDOI Listing

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