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Dive into the research topics where Justine Desroches is active.

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Featured researches published by Justine Desroches.


Angewandte Chemie | 2014

Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding

Pier Alexandre Champagne; Yasmine Benhassine; Justine Desroches; Jean-François Paquin

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 C-F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C-F bonds in the presence of other benzylic leaving groups.


Organic Letters | 2012

Halogenation of Primary Alcohols Using a Tetraethylammonium Halide/[Et2NSF2]BF4 Combination

Marie-France Pouliot; Olivier Mahé; Jean-Denys Hamel; Justine Desroches; Jean-François Paquin

The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et(2)NSF(2)]BF(4) (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.


Organic Letters | 2015

Introduction of the 4,4,4-trifluorobut-2-ene chain exploiting a regioselective Tsuji-Trost reaction catalyzed by palladium nanoparticles.

Rémy Hemelaere; Justine Desroches; Jean-François Paquin

A palladium-nanoparticle-catalyzed Tsuji-Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asymmetric dihydroxylation of a product were also examined.


Organic and Biomolecular Chemistry | 2016

Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols

Justine Desroches; Ariane Tremblay; Jean-François Paquin

The racemic and enantioselective metal-catalyzed addition of arylboronic acids to 4- and 3-(pentafluorosulfur)benzaldehydes is reported. The racemic synthesis was accomplished using a Pd-based system and a wide range of arylboronic acids could be used, resulting in yields of 42 to 98% of the corresponding SF5-containing diarylmethanols. A ruthenium-based system, along with (R,R)-Me-BIPAM as the chiral ligand, was investigated and optimized for the enantioselective version. In this case, while the chiral SF5-containing diarylmethanols were generally obtained in good yields (up to 94%) and enantioselectivities (up to 98% ee), limitations were also observed. For instance, 4-(pentafluorosulfur)benzaldehyde generally provided slightly better yields than 3-(pentafluorosulfur)benzaldehyde. In addition, lower yields and enantioselectivities were observed when using either 4- and 3-substituted arylboronic acids bearing electron-withdrawing (e.g., CO2Et, NO2, CF3) or 2-substituted arylboronic acids (regardless of the nature of the substituent). Overall, the SF5-containing diarylmethanols described herein represent novel and potentially useful fluorinated building blocks for the synthesis of biologically active compounds.


Beilstein Journal of Organic Chemistry | 2018

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

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

In recent years, the highly polar C–F bond has been utilised in activation chemistry despite its low reactivity to traditional nucleophiles, when compared to other C–X halogen bonds. Paquin’s group has reported extensive studies on the 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 an enantiopure isotopomer of benzyl fluoride to identify whether the reaction conditions favour a dissociative (SN1) or associative (SN2) pathway. [2H]-Isotopomer ratios in the reactions were assayed using the Courtieu 2H NMR method in a chiral liquid crystal (poly-γ-benzyl-L-glutamate) matrix and demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor.


Chemical Reviews | 2015

Monofluorination of Organic Compounds: 10 Years of Innovation

Pier Alexandre Champagne; Justine Desroches; Jean-Denys Hamel; Mathilde Vandamme; Jean-François Paquin


Synthesis | 2014

Organic Fluorine as a Hydrogen-Bond Acceptor: Recent Examples and Applications

Pier Alexandre Champagne; Justine Desroches; Jean-François Paquin


Organic and Biomolecular Chemistry | 2015

In situ activation of benzyl alcohols with XtalFluor-E: formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel–Crafts benzylation

Justine Desroches; Pier Alexandre Champagne; Yasmine Benhassine; Jean-François Paquin


European Journal of Organic Chemistry | 2013

Amide Formation Using In Situ Activation of Carboxylic Acids with [Et2NSF2]BF4

Olivier Mahé; Justine Desroches; Jean-François Paquin


Journal of Fluorine Chemistry | 2016

Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator

Rémy Hemelaere; Pier Alexandre Champagne; Justine Desroches; Jean-François Paquin

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David O'Hagan

University of St Andrews

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Neil S. Keddie

University of St Andrews

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