Chinese Journal of Organic Chemistry >
Synthesis of gem-Difluoroalkenes through Nickel-Promoted Electrochemical Reductive Cross-Coupling
Received date: 2021-08-06
Revised date: 2021-09-05
Online published: 2021-09-15
Supported by
National Natural Science Foundation of China(21732006); National Natural Science Foundation of China(51821006); National Natural Science Foundation of China(51961135104); Research Funds of the Double First-Class Initiative of University of Science and Technology of China(YD3530002002)
gem-Difluoroalkenes are important fluorine-containing compounds with structural superiority in organic synthetic chemistry and medicinal chemistry. For instance, the gem-difluoroethylene moiety could be converted to monofluoroalkenyl, difluoroalkyl, trifluoromethyl moiety, and many other fluorine-containing structures conveniently. The gem-difluoroethylene moiety is also an ideal carbonyl group bioisostere and has already been widely used in drug design. Herein, a nickel-promoted electrochemical reductive cross-coupling to access functionalized and substituted gem-difluoroalkenes is reported. This reaction enables the combination of allylic defluorination of trifluoromethyl alkenes and decarboxylation of redox-active esters or dehalogenation of alkyl halides under mild electrochemical reduction conditions and in an undivided cell, therefore obviates the use of stoichiometric amount metal powder or organic reductants. Furthermore, this reaction provides efficient access to biologically interesting molecules containing gem-difluoroethylene moiety.
Zhe Chang , Jiaxin Wang , Xi Lu , Yao Fu . Synthesis of gem-Difluoroalkenes through Nickel-Promoted Electrochemical Reductive Cross-Coupling[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 147 -159 . DOI: 10.6023/cjoc202108006
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