Journal ArticleDOI
Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of C ? F Bonds as Enabled by Hydrogen Bonding
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TLDR
A Friedel-Crafts benzylation of arenes with benzyl fluorides has been developed and produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid.Abstract:
A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.read more
Citations
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Journal ArticleDOI
Monofluorination of Organic Compounds: 10 Years of Innovation.
Pier Alexandre Champagne,Justine Desroches,Jean Denys Hamel,Mathilde Vandamme,Jean-François Paquin +4 more
Journal ArticleDOI
Hexafluoroisopropanol as a highly versatile solvent
TL;DR: In this paper, the main uses of hexafluoroisopropanol (HFIP) in the natural sciences and the underlying principles that give it such wide appeal are discussed. And the broad usage and beneficial effects in many areas of chemistry are shown.
Journal ArticleDOI
Rhodium-catalysed C( sp 2 )–C( sp 2 ) bond formation via C–H/C–F activation
TL;DR: A RhIII-catalysed tandem C–H/C–F activation for the synthesis of (hetero)arylated monofluoroalkenes and the employment of alcoholic solvent and the in-situ generated hydrogen fluoride are found to be beneficial in this transformation, indicating the possibility of the involvement of hydrogen bond activation mode with regards to the C–F bond cleavage step.
Journal ArticleDOI
Review of recent advances in CF bond activation of aliphatic fluorides
TL;DR: A review of the recent C F bond cleavage examples and further transformation of compounds bearing with an aliphatic fluoride, difluoromethylene group or trifluoricomethyl groups can be found in this paper.
Journal ArticleDOI
Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility.
Feng Hu,Mehulkumar Patel,Feixiang Luo,Carol R. Flach,Richard Mendelsohn,Eric Garfunkel,Huixin He,Michal Szostak +7 more
TL;DR: This work reports the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity.
References
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MonographDOI
The weak hydrogen bond : in structural chemistry and biology
TL;DR: In this paper, the weak hydrogen bond in supramolecular chemistry and biological structures is discussed. But weak and non-conventional hydrogen bonds are not considered in this paper.
Journal ArticleDOI
Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, .pi.*, .alpha., and .beta., and some methods for simplifying the generalized solvatochromic equation
TL;DR: In this article, a table of donnees (pour de nombreux solvants) des valeurs des parametres M*, α and β donnant respectivement la polarisabilite du solvant, son pouvoir de donneur de proton, and d'accepteur de protons dans les liaisons hydrogene solute-solvant
Journal ArticleDOI
Bond Dissociation Energies of Organic Molecules
TL;DR: In this paper, a list of reliable bond energies that are based on a set of critically evaluated experiments is provided and a brief description of the three most important experimental techniques for measuring bond energies is provided.
Journal Article
Bond dissociation energies of organic molecules
TL;DR: This Account presents a list of reliable bond energies that are based on a set of critically evaluated experiments and demonstrates how these experimental data can be applied to yield the heats of formation of organic radicals and the bond enthalpies of more than 100 representative organic molecules.
Journal ArticleDOI
C-F bond activation in organic synthesis.
Hideki Amii,Kenji Uneyama +1 more
TL;DR: Organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology and not only C-F bond formation but also selective C-f bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds.