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Search for "benzylic fluorides" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.

Benzylic C(sp3)–H fluorination

  • Alexander P. Atkins,
  • Alice C. Dean and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

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  • )–H functionalisation reactions in drug-discovery campaigns [17]. Although much is unknown about the precise details, several benzylic fluorides have been reported to be unstable, which is an effect that is apparently dependent on the substitution of the ring. While primary benzylic fluorides are
  • ). Overall, this work demonstrates the broadest range of secondary and tertiary benzylic substrates for electrochemical nucleophilic fluorination. As highlighted by the previous examples, electrochemical oxidation is a useful tool for preparing benzylic fluorides. However, a number of reports highlight the
  • and will hopefully encourage further development in key areas. This is particularly pertinent to the late-stage benzylic fluorination of complex molecules, which will require exceptionally mild conditions in order to tolerate a broad range of functional groups. A) Benzylic fluorides in bioactive
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Published 10 Jul 2024

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

  • Neil S. Keddie,
  • Pier Alexandre Champagne,
  • Justine Desroches,
  • Jean-François Paquin and
  • David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

Graphical Abstract
  • C–F activation of benzylic fluorides for nucleophilic substitutions and Friedel–Crafts reactions, using a range of hydrogen bond donors such as water, triols or hexafluoroisopropanol (HFIP) as the activators. This study examines the stereointegrity of the C–F activation reaction through the use of
  • demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor. Keywords: benzylic fluorides; C–F activation; chiral liquid crystal; 2H NMR; PBLG; stereochemistry; Introduction The C–F bond is the strongest
  • steric influence for backside attack of the nucleophile in the solvent-separated ion pair, arising from the large, congested hydrogen bond networks around the fluorine atom. C–F activation of benzylic fluorides to generate benzylamine or diarylmethane products. 7-[2H1]-(R)-Benzyl fluoride ((R)-1
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Full Research Paper
Published 09 Jan 2018

Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

  • Pier Alexandre Champagne,
  • Alexandre Saint-Martin,
  • Mélina Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2013, 9, 2451–2456, doi:10.3762/bjoc.9.283

Graphical Abstract
  • C–F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run
  • under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields. Keywords: C–F bond activation; highly concentrated
  • and resulted in a higher isolated yield (Table 3, entry 1). Reactions of secondary benzylic fluorides were unfortunately untractable, and primary aliphatic amines (i.e. n-butylamine) generated a mixture of inseparable mono- and dibenzylation products (see Supporting Information File 1 for details
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Published 13 Nov 2013
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