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Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

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Abstract

We describe a nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides. A unique catalytic cycle merging alkyl nickel chain-walking and defluorinative coupling enables the introduction of a broad array of fluoroalkenyl moieties into carbon chains. Control experiments with other halogenated alkenes demonstrated the essential role of fluorine atoms in this reaction. Notably, the reaction proceeds under mild conditions and allows for the synthesis of a variety of valuable monofluoroalkenes.

Graphical abstract: Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

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Publication details

The article was received on 19 Sep 2018, accepted on 08 Nov 2018 and first published on 09 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC04162H
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

    L. Zhou, C. Zhu, P. Bi and C. Feng, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04162H

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