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Stereodivergent hydrodefluorination of gem-difluoroalkenes: selective synthesis of (Z)- and (E)-monofluoroalkenes

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Abstract

We have developed a novel approach for the stereodivergent hydrodefluorination of gem-difluoroalkenes using copper(I) catalysts to obtain stereodefined monofluoroalkenes. Both (Z)- and (E)-terminal monofluoroalkenes were obtained by the hydrodefluorination of gem-difluoroalkenes in the presence of copper(I) catalysts and diboron or hydrosilane, respectively, with high stereoselectivity. DFT calculations were conducted to elucidate the stereoselectivity.

Graphical abstract: Stereodivergent hydrodefluorination of gem-difluoroalkenes: selective synthesis of (Z)- and (E)-monofluoroalkenes

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Publication details

The article was received on 07 Jul 2017, accepted on 31 Aug 2017 and first published on 01 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC05225A
Citation: Chem. Commun., 2017, Advance Article
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    Stereodivergent hydrodefluorination of gem-difluoroalkenes: selective synthesis of (Z)- and (E)-monofluoroalkenes

    R. Kojima, K. Kubota and H. Ito, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC05225A

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