Justine Desroches
Laval University
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Publication
Featured researches published by Justine Desroches.
Angewandte Chemie | 2014
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
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
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
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
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
Pier Alexandre Champagne; Justine Desroches; Jean-Denys Hamel; Mathilde Vandamme; Jean-François Paquin
Synthesis | 2014
Pier Alexandre Champagne; Justine Desroches; Jean-François Paquin
Organic and Biomolecular Chemistry | 2015
Justine Desroches; Pier Alexandre Champagne; Yasmine Benhassine; Jean-François Paquin
European Journal of Organic Chemistry | 2013
Olivier Mahé; Justine Desroches; Jean-François Paquin
Journal of Fluorine Chemistry | 2016
Rémy Hemelaere; Pier Alexandre Champagne; Justine Desroches; Jean-François Paquin