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

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.

SUBMITTER: Zhou L

PROVIDER: S-EPMC6349022 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with <i>gem</i>-difluoroalkenes.

Zhou Lu L Zhu Chuan C Bi Peijia P Feng Chao C

Chemical science 20181109 4

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 synthes ...[more]

PMID: 30774912

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