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Photoredox Activation of Fluorinated Organozinc Reagents: Hydrofluoroalkylation of Unactivated and Electron Deficient Alkenes. | LitMetric

AI Article Synopsis

  • The process involves hydrofluoroalkylating alkenes using organozinc reagents powered by photocatalysis.
  • Fluorinated alkyl radicals are formed through the single electron oxidation of the carbon-zinc bond in these reagents.
  • The addition of these radicals to alkenes is completed either by transferring a hydrogen atom for less reactive olefins or through a reduction/protonation method for more reactive compounds like arylidenemalononitriles.

Article Abstract

Hydrofluoroalkylation of alkenes with organozinc reagents under photocatalytic conditions is described. The fluorinated alkyl radicals were generated from organozincs by the single electron oxidation of the carbon-zinc bond. The radical addition step is followed either by hydrogen atom transfer for unactivated olefins or by a reduction/protonation sequence for strongly accepting arylidenemalononitriles.

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Source
http://dx.doi.org/10.1021/acs.joc.4c01623DOI Listing

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