Groupe de recherche en chimie organique et médicinale

Jean-François Paquin

Publications

Articles

2017

  1. Hamel, J.-D.; Hayashi, T.; Cloutier, M.; Savoie, P. R.; Thibeault, O.; Paquin, J.-F. Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Organic & Biomolecular Chemistry, 2017, en ligne.

  2. Hamel, J.-D.; Beaudoin, M.; Cloutier, M.; Paquin, J.-F. Hydrogen-Bond-Promoted Friedel–Crafts Reaction of Secondary Propargylic Fluorides: Preparation of 1-Alkyl-1-aryl-2-alkynes. Synlett, 2017, en ligne.

  3. Gagnon, M.-C.; Dautrey, S.; Bertrand, X.; Auger, M.; Paquin, J.-F. A Flexible Synthetic Approach to Phosphatidylglycerols. European Journal of Organic Chemistry, 2017, 6401-6407.

  4. Desroches, J; Gilbert, A.; Houle, C.; Paquin, J.-F. A Radical Access to CF3- and SF5-Containing Dihydrobenzofurans and Indolines. Synthesis, 2017, 49, 4827-4844.

  5. Vandamme, M.; Paquin, J.-F. Eliminative Deoxofluorination Using XtalFluor-E: A One-Step Synthesis of Monofluoroalkenes from Cyclohexanone Derivatives. Organic Letters, 2017, 19, 3604-3607.

  6. Barbeau, X.; Mathieu, P.; Paquin, J.-F.; Lagüe, P. Characterization of the structure, dynamics and allosteric pathways of human NPP1 in its free form and substrate–bound complex from molecular modeling. Molecular BioSystems, 2017, 13, 1058-1069.

  7. Gagnon, M.-C.; Strandberg, E.; Grau-Campistany, A.; Wadhwani, P.; Reichert, J.; Bürck, J.; Rabanal. F.; Auger, M.; Paquin, J.-F.; Ulrich, A. S. Influence of the length and charge on the activity of α-helical amphipathic antimicrobial peptides. Biochemistry, 2017, 56, 1680-1695.

  8. Drouin, M.; Tremblay, S.; Paquin, J.-F. Palladium-catalyzed synthesis of monofluoroalkenes from 3,3-difluoropropenes using dimethylmalonate and derivatives as nucleophiles. Organic & Biomolecular Chemistry, 2017, 15, 2376-2384.

  9. Lebleu, T.; Paquin, J.-F. Direct allylation of benzyl alcohols, diarylmethanols, and triarylmethanols mediated by XtalFluor-E. Tetrahedron Letters, 2017, 58, 442-444.

  10. Lefebvre, C.-A.; Forcellini, E.; Boutin, S.; Côté, M.-F.; C.-Gaudreault, R.; Mathieu, P.; Lagüe, P.; Paquin, J.-F. Synthesis of novel substituted pyrimidine derivatives bearing a sulfamide group and their in vitro cancer growth inhibition activity. Bioorganic & Medicinal Chemistry, 2017, 27, 299-302.

2016

  1. Vandamme, M.; Bouchard, L.; Gilbert, A.; Keita, M.; Paquin, J.-F. Direct esterification of carboxylic acids with perfluorinated alcohols mediated by XtalFluor-E. Organic Letters, 2016, 18, 6468-6471.

  2. Desroches, J.; Tremblay, A.; Paquin, J.-F. Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols. Organic & Biomolecular Chemistry, 2016, 14, 8764–8780.

  3. Desroches, J.; Forcellini, E.; Paquin, J.-F. Complementary Methods for the Introduction of the (E)-3-(Pentafluorosulfanyl)allyl Chain unto O-, N-, S-, and C-Based Nucleophiles. European Journal of Organic Chemistry, 2016, 4611–4620.

  4. Hemelaere, R.; Champagne, P. A.; Desroches, J.; Paquin, J.-F. Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator. Journal of Fluorine Chemistry, 2016, 190, 1–6.

  5. Hamel, J.-D.; Cloutier, M.; Paquin, J.-F. Exploiting a Difference in Leaving Group Ability: An Approach to β-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes. Organic Letters, 2016, 18, 1852–1855.

  6. Drouin, M.; Hamel, J.-D.; Paquin, J.-F. Exploiting 3,3-Difluoropropenes for the Synthesis of Monofluoroalkenes. Synlett, 2016 27, 821–830.

2015

  1. Forcellini, E.; Hemelaere, R.; Desroches, J.; Paquin, J.-F. Systematic Study of the Reactivity of (E)-4,4,4-trifluorobut-2-en-1-yl 4-methylbenzenesulfonate Towards Different Classes of Nucleophiles. Journal of Fluorine Chemistry, 2015, 180, 216–221.

  2. Keita, M.; Vandamme, M.; Paquin, J.-F. Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E. Synthesis, 2015, 47, 3758–3766.

  3. Chatalova Sazepin, C.; Hemelaere, R.; Paquin, J.-F.; Sammis, G. Recent Advances in Radical Fluorination. Synthesis, 2015, 47, 2554–2569.

  4. Shayhidin, E. E.; Forcellini, E.; Boulanger, M.-C.; Mahmut, A.; Dautrey, S.; Barbeau, X.; Lagüe, P.; Sévigny, J.; Paquin, J.-F.; Mathieu, P. Quinazolin-4-piperidine Sulfamides are Specific Inhibitors of Human NPP1 and Prevent Pathologic Mineralization of Valve Interstitial Cells. British Journal of Pharmacology, 2015, 172, 4189–4199.

  5. Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Monofluorination of Organic Compounds: 10 Years of Innovation. Chemical Reviews, 2015, 115, 9073–9174.

  6. Hamel, J.-D.; Drouin, M.; Paquin, J.-F. Synthesis of Monofluoroalkenes using a Pt-Catalyzed Amination Reaction of Cyclic 3,3-Difluoropropenes with Secondary Aliphatic Amines. Journal of Fluorine Chemistry, 2015, 174, 81–87.

  7. Hemelaere, R.; Desroches, J.; Paquin, J.-F. Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji–Trost Reaction Catalyzed by Palladium Nanoparticles. Organic Letters, 2015, 17, 1770–1773.

  8. Desroches, J.; Champagne, P. A.; Benhassine, Y.; Paquin, J.-F. In Situ Activation of Benzyl Alcohols with XtalFluor-E: Formation of 1,1-Diarylmethanes and 1,1,1-Triarylmethanes Through Friedel-Crafts Benzylation. Organic & Biomolecular Chemistry, 2015, 13, 2243–2246.

  9. Champagne, P. A.; Drouin, M.; Legault, C. Y.; Audubert, C.; Paquin, J.-F. Revised mechanistic explanation for the alcohol-promoted amination of benzylic fluorides under highly concentrated conditions: Computational and experimental evidence on a model substrate. Journal of Fluorine Chemistry, 2015, 171, 113–119.

  10. Keïta, M.; Vandamme, M.; Mahé, O.; Paquin, J.-F. Synthesis of isocyanides through dehydration of formamides using XtalFluor-E. Tetrahedron Letters, 2015, 56, 461–464.

  11. Champagne, P. A.; Desroches, J.; Paquin, J.-F. Organic Fluorine as a Hydrogen-Bond Acceptor: Recent Examples and Applications. Synthesis, 2015, 47, 306–322.

2014

  1. Champagne, P. A.; Benhassine, Y.; Desroches, J.; Paquin, J.-F. Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of C–F Bonds as Enabled by Hydrogen Bonding. Angewandte Chemie International Edition, 2014, 53 13835–13839.

  2. Gagnon, M.-C.; Turgeon, B.; Savoie, J.-D.; Parent, J.-F.; Auger, M.; Paquin, J.-F. Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines. Organic and Biomolecular Chemistry, 2014, 12, 5126–5135.

  3. Rueda-Becerril, M.; Mahé, O.; Drouin, M.; Majewski, M. B.; West, J. G.; Wolf, M. O.; Sammis, G. M.; Paquin, J.-F. Direct C–F Bond Formation Using Photoredox Catalysis. Journal of the American Chemical Society, 2014, 136, 2637–2641.

2013

  1. Champagne, P. A.; Saint-Martin, A.; Drouin, M.; Paquin, J.-F. Triol-Promoted Activation of C–F Bonds: Amination of Benzylic Fluorides Under Highly Concentrated Conditions Mediated by 1,1,1-Tris(hydroxymethyl)propane. Beilstein Journal of Organic Chemistry, 2013, 9, 2451–2456.

  2. Mahé, O.; L'Heureux, A.; Couturier, M.; Bennett, C.; Clayton, S.; Tovell, D.; Beaulieu, F.; Paquin, J.-F. Deoxofluorination Reactions Using N,N-Disubstituted Aminodifluorosulfinium Tetrafluoroborate Salts. Journal of Fluorine Chemistry, 2013, 153, 57–60.

  3. Turcotte-Savard, M.-O.; Mahé, O.; Paquin, J.-F. Dialkylaminodifluorosulfinium Tetrafluoroborate Salts: Synthesis and Applications. Chimica Oggi-Chemistry Today, 2013, 31, 14–19.
  4. Mahé, O.; Desroches, J.; Paquin, J.-F. Amide Formation Using In Situ Activation of Carboxylic Acids with [Et2NSF2]BF4. European Journal of Organic Chemistry, 2013, 4325–4331.

  5. Champagne, P. A.; Pomarole, J.; Thérien, M.-E.; Benhassine, Y.; Beaulieu, S.; Legault, C. Y.; Paquin, J.-F. Enabling Nucleophilic Substitution Reaction of Activated Alkyl Fluorides Through Hydrogen-Bonding. Organic Letters, 2013, 15, 2210–2213.

  6. Malo-Forest, B.; Landelle, G.; Roy, J.-A.; Lacroix, J.; C.-Gaudreault, R.; Paquin, J.-F. Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen. Bioorganic & Medicinal Chemistry Letters 2013, 23, 1712–1715.

  7. Turcotte-Savard, M.-O.; Paquin, J.-F. Efficient synthesis of silylated 2,2-difluorostyrene derivatives through Suzuki-Miyaura cross-coupling of 2,2-difluoro-1-iodo-1-silylethenes. Organic & Biomolecular Chemistry 2013, 11, 1367–1375.

  8. Malo-Forest, B.; Roy, J.-A.; Paquin, J.-F. Bromination/desilicobromination of silylated monofluoroalkenes using tetrabutylammonium tribromide under microwave conditions. Journal of Fluorine Chemistry 2013, 145, 77–80.

2012

  1. Bergeron, M.; Guyader, D.; Paquin, J.-F. SN2’ Reaction of Allylic Difluorides with Lithium Amides and Thiolates. Organic Letters 2012, 14, 5888–5891. (L'importance de cet article a été soulignée dans Synfacts 2013, 9, 311.)

  2. Pouliot, M.-F.; Mahé, O.; Hamel, J.-D.; Desroches, J.; Paquin, J.-F. Halogenation of Primary Alcohols Using a Tetraethylammonium Halide/[Et2NSF2]BF4 Combination. Organic Letters 2012, 14, 5428–5431.

  3. Leung, J. C. T.; Chatalova Sazepin, C.; West, J. G.; Rueda-Becerril, M.; Paquin, J.-F.; Sammis, G. M. Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids. Angewandte Chemie International Edition 2012, 51, 10804–10807.

  4. Pouliot, M.-F.; Angers, L.; Hamel, J.-D.; Paquin, J.-F. Synthesis of 2-Oxazolines and Related N-Containing Heterocycles Using [Et2NSF2]BF4 as a Cyclodehydration Agent. Tetrahedron Letters 2012, 53, 4121–4123.

  5. Rueda-Becerril, M.; Chatalova Sazepin, C.; Leung, J. C. T.; Okbinoğlu, T.; Kennepohl, P.; Paquin, J.-F.; Sammis, G. M. Fluorine Transfer to Alkyl Radicals. Journal of the American Chemical Society 2012, 134, 4026–4029.

  6. Guimond-Tremblay, J.; Gagnon, M.-C.; Pineault-Maltais, J.-A.; Turcotte, V.; Auger, M.; Paquin, J.-F. Synthesis and Properties of Monofluorinated Dimyristoylphosphatidylcholine Derivatives: Potential Fluorinated Probes for the Study of Membrane Topology. Organic & Biomolecular Chemistry 2012, 10, 1145–1148.

  7. Pouliot, M.-F.; Angers, L.; Hamel, J.-D.; Paquin, J.-F. Synthesis of 1,3,4-Oxadiazoles from 1,2-Diacylhydrazines using [Et2NSF2]BF4 as a Practical Cyclodehydration Agent. Organic & Biomolecular Chemistry 2012, 10, 988–993.

  8. Chénard, S.; Barberis, C.; Otis, F.; Paquin, J.-F.; Martel, J.; Banville, C.; Voyer, N. Synthesis of an Anion-binding Amino Acid. Tetrahedron Letters 2012, 53, 409–411.

  9. Bélanger, É.; Pouliot, M.-F.; Courtemanche, M.-A.; Paquin, J.-F. Design, Synthesis and Applications of Potential Substitutes to t-Bu-PHOX in Pd-Catalyzed Asymmetric Transformations and Their Use for the Improvement of the Enantioselectivity in the Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates. The Journal of Organic Chemistry 2012, 77, 317–331.

2011

  1. Bergeron, M.; Johnson, T.; Paquin, J.-F. The Use of Fluoride as a Leaving Group: SN2' Displacement of a C-F Bond on 3,3-Difluoropropenes with Organolithium Reagents To Give Access to Monofluoroalkenes. Angewandte Chemie International Edition 2011, 50, 11112–11116. (L'importance de cet article a été soulignée dans Synfacts 2012, 8, 206.)

  2. Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Synthetic Approaches to Monofluoroalkenes. Compte-rendu invité dans Chemical Society Reviews 2011, 40, 2867–2908.

  3. Landelle, G.; Turcotte-Savard, M.-O.; Angers, L.; Paquin, J.-F. Stereoselective Synthesis of Both Isomers of β-Fluorostyrene Derivatives from a Common Intermediate. Organic Letters 2011, 13, 1568–1571.

  4. Paquin, J.-F. Synthesis of Monofluoroalkenes via the Activation of Allylic C-F Bonds: a Novel Route to β-Aminofluoroalkenes using a Pd-Catalyzed Allylic Amination Reaction of 3,3-Difluoropropenes. Contribution invitée dans Synlett 2011, 289–293.

2010

  1. Pigeon, X.; Bergeron, M.; Barabé, F.; Dubé, P.; Frost, H. N.; Paquin, J.-F. Activation of Allylic C-F bonds: Pd-Catalyzed Allylic Amination Reaction of 3,3-difluoropropenes. Angewandte Chemie International Edition 2010, 49, 1123–1127.

2009

  1. Landelle, G.; Turcotte-Savard, M.-O.; Marterer, J.; Champagne, P. A. Paquin, J.-F. Stereocontrolled Access to Unsymmetrical 2-Fluoro-1,1-diarylethenes. Organic Letters 2009, 11, 5406–5409.

  2. Bélanger, É.; Pouliot, M.-F.; Paquin, J.-F. The Use of 5,5-(dimethyl)-i-Pr-PHOX as a Practical Equivalent to t-Bu-PHOX in Asymmetric Catalysis. Organic Letters 2009, 11, 2201–2204.

  3. Landelle, G.; Champagne, P. A.; Barbeau, X.; Paquin, J.-F. Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetra-Substituted Fluoroalkenes. Organic Letters 2009, 11, 681–684.

2008

  1. Bélanger, É.; Houzé, C.; Guimond, N. Cantin, K.; Paquin, J.-F. Enantioselective Pd-Catalyzed Allylation of Fluorinated Enol Carbonates: Unexpected Importance of the Metal-to-Chiral Ligand Ratio. Chemical Communications 2008, 3254–3253. (L'importance de cet article a été soulignée dans Synfacts 2008, 9, 960.)

2007

  1. Bélanger, É.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J.-F. Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers. Journal of the American Chemical Society 2007, 129, 1034–1035.

2006

  1. Chau, A.; Paquin, J.-F.; Lautens, M. Diastereoselective Palladium-Catalyzed Formate Reduction of Allylic Carbonates en route to Polypropionate Systems. Journal of Organic Chemistry 2006, 71, 1924–1933.

2005

  1. Paquin, J.-F.; Stephenson, C. R. J.; Defieber, C.; Carreira, E. M. Catalytic Asymmetric Synthesis with Rh-Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated Esters. Organic Letters 2005, 7, 3821–3824.
  2. Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene-Rhodium Catalysts. Journal of the American Chemical Society 2005, 127, 10850–10851.
  3. Alberico, D.; Paquin, J.-F.; Lautens, M. Palladium-Catalyzed Sequential Alkylation-Alkenylation Reactions: Application Towards the Synthesis of Polyfunctionalized Fused Aromatic Rings. Tetrahedron 2005, 61, 6283–6297.

2004

  1. Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors. Organic Letters 2004, 6, 3873–3876.

2003

  1. Lautens, M.; Paquin, J.-F. Diastereoselective Palladium-Catalyzed Formate Reduction of Allylic Carbonates as a New Entry into Propionate Units. Organic Letters 2003, 5, 3391–3394.

2002

  1. Lautens, M.; Paquin, J.-F. ; Piguel, S. Palladium-Catalyzed Sequential Alkylation-Alkenylation Reactions. Application to the Synthesis of 2-Substituted-4-Benzoxepines and 2,5-Disubstituted-4-Benzoxepines. Journal of Organic Chemistry 2002, 67, 3972–3974.

2001

  1. Lautens, M.; Paquin, J.-F.; Piguel, S.; Dahlmann, M. Palladium-Catalyzed Sequential Alkylation-Alkenylation Reactions and their Application to the Synthesis of Fused Aromatic Rings. Journal of Organic Chemistry 2001, 66, 8127–8134.

Chapitres de livre

  1. Champagne, P. A.; Drouin, M.; Paquin, J.-F. Benzylic fluorides (Update 2016). Dans Science of Synthesis, Knowledge Updates 2016. Bagley, M. C.; Paquin, J.-F., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2016; pp. 419-449.
  2. Hamel, J.-D.; Paquin, J.-F. Propargylic fluorides (Update 2016). Dans Science of Synthesis, Knowledge Updates 2016. Bagley, M. C.; Paquin, J.-F., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2016; pp. 409-418.
  3. Vandamme, M.; Paquin, J.-F. Synthesis by substitution of hydroxy groups in alcohols (Update 2016). Dans Science of Synthesis, Knowledge Updates 2016. Bagley, M. C.; Paquin, J.-F., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2016; pp. 395-408.
  4. Desroches, J.; Paquin, J.-F. Synthesis by substitution of carbon functionalities (Update 2016). Dans Science of Synthesis, Knowledge Updates 2016. Bagley, M. C.; Paquin, J.-F., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2016; pp. 375-393.
  5. Mahé, O.; Paquin, J.-F. Diethylaminodifluorosulfinium Tetrafluoroborate (XtalFluor-E®). Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2013; en ligne.
  6. Mahé, O.; Paquin, J.-F. Morpholinodifluorosulfinium Tetrafluoroborate (XtalFluor-M®). Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2013; en ligne.
  7. Champagne, P. A.; Paquin, J.-F. Trifluoro(N-methylmethanaminato)sulfur. Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2013; en ligne.
  8. Paquin, J.-F. Fluorination of organic compounds. Dans McGraw-Hill Yearbook of Science & Technology 2013. McGraw-Hill Professional: New-York, 2013; pp. 147-150.
  9. Landelle, G.; Paquin, J.-F. Conjugate Addition of α,β-Unsaturated Esters. Dans Science of Synthesis Knowledge Update. Carreira, E. M., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2011; sous presse.
  10. Landelle, G.; Paquin, J.-F. Synthesis with Retention of the Functional Group (Update 1). Dans Science of Synthesis Knowledge Update. Carreira, E. M., Éd. Georg Thieme Verlag KG: Stuttgart-New York, 2010; pp. 277-282.
  11. Landelle, G.; Paquin, J.-F. Fluoroiodomethane. Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2010; en ligne.
  12. Bélanger, É.; Paquin, J.-F. Allyl Acetate. Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2010; en ligne.
  13. Turcotte-Savard, M.-O.; Paquin, J.-F. Zinc Floride. Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2010; en ligne.
  14. Alberico, D.; Paquin, J.-F. Norbornene. Dans Electronic Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Éd. John Wiley & Sons Ltd.: Chichester, 2008; en ligne.
  15. Paquin, J.-F.; Lautens, M. Allylic Substitution Reactions. Chapitre invité dans Comprehensive Asymmetric Catalysis, supplement #2. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Éds; Springer-Verlag: Berlin, 2003; pp. 73–95.