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Issue 20, 2016
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The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations

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Abstract

Fluoroalkylation reaction, featuring the transfer of a fluoroalkyl group to a substrate, is a straightforward and efficient method for the synthesis of organofluorine compounds. In fluoroalkylation reactions, fluorine substitution can dramatically influence the chemical outcome. On the one hand, the chemistry of alkylation with non-fluorinated reagents may not be applicable to fluoroalkylations, so it is necessary to tackle the fluorine effects to achieve efficient fluoroalkylation reactions. On the other hand, fluorine substitution may bring about new reactivities and transformations that cannot be realized in alkylation with non-fluorinated reagents; thus, fluorine substitution can be used to explore new synthetic methods. This tutorial review provides a brief overview of the unique fluorine effects in recently developed nucleophilic, electrophilic, radical, and transition metal-mediated fluoroalkylation reactions by comparing with either their non-fluorinated counterparts or fluorinated counterparts with different numbers of fluorine substituents.

Graphical abstract: The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations

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Publication details

The article was received on 30 Apr 2016 and first published on 08 Aug 2016


Article type: Tutorial Review
DOI: 10.1039/C6CS00351F
Citation: Chem. Soc. Rev., 2016,45, 5441-5454
  • Open access: Creative Commons BY license
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    The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations

    C. Ni and J. Hu, Chem. Soc. Rev., 2016, 45, 5441
    DOI: 10.1039/C6CS00351F

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