Pier Alexandre Champagne
Pier Alexandre Champagne
(Pier Alexandre Champagne) Assistant Professor, Chemistry and Environmental Science
354 Tiernan Hall (TIER)
Education
Ph.D.; Université Laval; Organic Chemistry; 2015
B.S.; Université Laval; Chemistry; 2010
B.S.; Université Laval; Chemistry; 2010
Past Courses
CHEM 243: ORGANIC CHEMISTRY I
CHEM 244: ORGANIC CHEMISTRY II
CHEM 244: ORGANIC CHEMISTRY II - HONORS
CHEM 244A: ORGANIC CHEMISTRY II LAB
CHEM 605: ADV ORGANIC CHEM: STRUCTR
CHEM 605: ADVANCED ORGANIC CHEMISTRY I: STRUCTURE
CHEM 791: GRADUATE SEMINAR
CHEM 792B: PRE-DOCTORAL RESEARCH
CHEM 792C: PRE-DOCTORAL RESEARCH
EVSC 791: ENVIRONMENTAL SCIENCE SEMINAR
CHEM 244: ORGANIC CHEMISTRY II
CHEM 244: ORGANIC CHEMISTRY II - HONORS
CHEM 244A: ORGANIC CHEMISTRY II LAB
CHEM 605: ADV ORGANIC CHEM: STRUCTR
CHEM 605: ADVANCED ORGANIC CHEMISTRY I: STRUCTURE
CHEM 791: GRADUATE SEMINAR
CHEM 792B: PRE-DOCTORAL RESEARCH
CHEM 792C: PRE-DOCTORAL RESEARCH
EVSC 791: ENVIRONMENTAL SCIENCE SEMINAR
In Progress
Experimental and computational investigations on elemental sulfur for organic chemistry
Experimental and computational studies on the reaction mechanisms and reactivity profile of elemental sulfur. This project targets the reactivity of sulfur with nucleophiles, elucidating mechanisms of known reactions and developing new chemical transformations for the synthesis of value-added sulfur-containing molecules.
Mechanisms and origins of selectivity for phase-transfer catalyzed reactions
In this computational project, state-of-the-art Density Functional Theory (DFT) calculations are used to elucidate the mechanisms and origins of enantioselectivity of asymmetric transformations catalyzed by chiral phase-transfer catalysts. Specifically, we are interested in reactions that do not use enolate nucleophiles. The goal is to develop a comprehensive model of reactivity and selectivity for these catalysts, allowing further rational developments in the field.
Rearrangements and reactivity of complex non-classical cations
Non-classical cations are unique chemical structures that are poorly understood, but participate in many reactions involving carbocations. In this project, DFT calculations are used to probe the various rearrangements and reactivity patterns of such carbocations, in addition to probing the role of substitution on these pathways.
Experimental and computational studies on the reaction mechanisms and reactivity profile of elemental sulfur. This project targets the reactivity of sulfur with nucleophiles, elucidating mechanisms of known reactions and developing new chemical transformations for the synthesis of value-added sulfur-containing molecules.
Mechanisms and origins of selectivity for phase-transfer catalyzed reactions
In this computational project, state-of-the-art Density Functional Theory (DFT) calculations are used to elucidate the mechanisms and origins of enantioselectivity of asymmetric transformations catalyzed by chiral phase-transfer catalysts. Specifically, we are interested in reactions that do not use enolate nucleophiles. The goal is to develop a comprehensive model of reactivity and selectivity for these catalysts, allowing further rational developments in the field.
Rearrangements and reactivity of complex non-classical cations
Non-classical cations are unique chemical structures that are poorly understood, but participate in many reactions involving carbocations. In this project, DFT calculations are used to probe the various rearrangements and reactivity patterns of such carbocations, in addition to probing the role of substitution on these pathways.
Journal Article
Sharma, Jyoti , & Champagne, Pier Alexandre (2024). Mechanisms of the Gewald synthesis of 2-aminothiophenes from elemental sulfur. The Journal of Organic Chemistry, 89, 9609-9619.
Larmore, Sean P, & Champagne, Pier Alexandre (2024). Substituent effects on the equilibria between cyclopropylcarbinyl, bicyclobutonium, homoallyl, and cyclobutyl cations. The Journal of Organic Chemistry, 89, 8146-8156.
Fosnacht, Kaylin, & Sharma, Jyoti, & Champagne, Pier Alexandre, & Pluth, Michael D (2024). Transpersulfidation or H2S Release? Understanding the Landscape of Persulfide Chemical Biology. Journal of the American Chemical Society, 146, 18689-18698.
Larmore, Sean P, & Champagne, Pier Alexandre (2023). Cyclopropylcarbinyl-to-Homoallyl Carbocation Equilibria Influence the Stereospecificity in the Nucleophilic Substitution of Cyclopropylcarbinols. Journal of Organic Chemistry, 88(11), 6947-6954.
Newton, Turner D., & Li, Keyan, & Sharma, Jyoti, & Champagne, Pier, & Pluth, Michael D. (2023). Direct hydrogen selenide (H2Se) release from activatable selenocarbamates. Chemical Science, 14(27), 7581-7588.
Larmore, Sean P, & Champagne, Pier Alexandre (2024). Substituent effects on the equilibria between cyclopropylcarbinyl, bicyclobutonium, homoallyl, and cyclobutyl cations. The Journal of Organic Chemistry, 89, 8146-8156.
Fosnacht, Kaylin, & Sharma, Jyoti, & Champagne, Pier Alexandre, & Pluth, Michael D (2024). Transpersulfidation or H2S Release? Understanding the Landscape of Persulfide Chemical Biology. Journal of the American Chemical Society, 146, 18689-18698.
Larmore, Sean P, & Champagne, Pier Alexandre (2023). Cyclopropylcarbinyl-to-Homoallyl Carbocation Equilibria Influence the Stereospecificity in the Nucleophilic Substitution of Cyclopropylcarbinols. Journal of Organic Chemistry, 88(11), 6947-6954.
Newton, Turner D., & Li, Keyan, & Sharma, Jyoti, & Champagne, Pier, & Pluth, Michael D. (2023). Direct hydrogen selenide (H2Se) release from activatable selenocarbamates. Chemical Science, 14(27), 7581-7588.
SHOW MORE
Sharma, Jyoti, & Champagne, Pier (2023). Mechanisms of the Reaction of Elemental Sulfur and Polysulfides with Cyanide and Phosphines. Chemistry – A European Journal, 29(32),
Ribéraud, Maxime, & Porte, Karine, & Chevalier, Arnaud, & Madegard, Léa, & Rachet, Aurélie, & Delaunay-Moisan, Agnès, & Vinchon, Florian, & Thuéry, Pierre, & Chiappetta, Giovanni, & Champagne, Pier, & Pieters, Grégory, & Audisio, Davide, & Taran, Frédéric (2023). Fast and Bioorthogonal Release of Isocyanates in Living Cells from Iminosydnones and Cycloalkynes. Journal of the American Chemical Society, 145(4), 2219-2229.
Sharma, Jyoti, & Champagne, Pier Alexandre (2022). Benchmark of density functional theory methods for the study of organic polysulfides. Journal of Computational Chemistry, 43(32), 2131-2138.
Birepinte, Mélodie, & Champagne, Pier Alexandre, & Paquin, Jean-François (2022). Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes. Angewandte Chemie International Edition, 61(1), e202112575.
Feng, Minghao, & Madegard, Léa, & Riomet, Margaux, & Louis, Manon, & Champagne, Pier, & Pieters, Grégory, & Audisio, Davide, & Taran, Frédéric (2022). Selective chlorination of iminosydnones for fast release of amide, sulfonamide and urea-containing drugs. Chemical Communications, 58(61), 8500--8503.
Buttard, Floris, & Champagne, Pier (2022). Binding Modes and Origins of Enantioselectivity in the Phase-Transfer-Catalyzed Conjugate Cyanation of $\beta$-Trifluoromethylated Chalcones. ACS Catalysis, 12(14), 8185--8194.
Nnamdi, Fred U, & Diner, Colin, & Champagne, Pier, & Organ, Michael G (2021). Experimental and Computational Study on the Anti-Markovnikov Hydrofunctionalization of Olefins Using Glycine-Extended AQ-Auxiliaries.. Chemistry - A European Journal, 27(11), 3855--3860.
Yen-Pon, Expédite, & Buttard, Floris, & Fr\'ed\'eric, Lucas, , & Thuéry, Pierre, & Taran, Frédéric, & Pieters, Grégory, & Champagne, Pier, & Audisio, Davide (2021). Heterohelicenes through 1, 3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal. JACS Au, 1, 807-818.
Champagne, Pier (2021). Identifying the true origins of selectivity in chiral phosphoric acid catalyzed N-acyl-azetidine desymmetrizations. Chemical Science, 12, 15662-15672.
Buttard, Floris, & Sharma, Jyoti, & Champagne, Pier (2021). Recent advances in the stereoselective synthesis of acyclic all-carbon tetrasubstituted alkenes. Chemical Communications, 57, 4071-4088.
Liu, Chengyuan, & Wang, Qi, & Hivick, Brian E, & Ai, Yongling, & Champagne, Pier, & Pan, Yang, & Chen, Hao (2020). Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry. Analytical Chemistry, 92(23), 15291--15296.
Houle, Camille, & Savoie, Paul R, & Davies, Clotilde, & Jardel, Damien, & Champagne, Pier, & Bibal, Brigitte, & Paquin, Jean-Fran\ccois, (2020). Thiourea-catalyzed C--F Bond Activation: Amination of Benzylic Fluorides. Chemistry--A European Journal, 26(46), 10620--10625.
Sinha, Narayan, & Champagne, Pier, & Rodriguez, Michael J, & Lu, Yu, & Kopach, Michael E, & Mitchell, David, & Organ, Michael G (2019). One-Pot Sequential Kumada--Tamao--Corriu Couplings of (Hetero) Aryl Polyhalides in the Presence of Grignard-Sensitive Functional Groups Using Pd-PEPPSI-IPentCl. Chemistry--A European Journal, 25(26), 6508--6512.
Yen-Pon, Exp\'edite, , & Champagne, Pier, & Plougastel, Lucie, & Gabillet, Sandra, & Thu\'ery, Pierre, , & Johnson, Mizuki, & Muller, Gilles, & Pieters, Gr\'egory, , & Taran, Fr\'ed\'eric, , & Houk, Kendall N, & others, (2019). Sydnone-Based Approach to Heterohelicenes through 1, 3-Dipolar-Cycloadditions. Journal of the American Chemical Society, 141(4), 1435--1440.
Lombardi, Christopher, & Rucker, Richard P., & Froese, Robert D. J., & Sharif, Sepideh, & Champagne, Pier, & Organ, Michael G. (2019). Rate and Computational Studies for Pd-NHC-Catalyzed Amination with Primary Alkylamines and Secondary Anilines: Rationalizing Selectivity for Monoarylation versus Diarylation with NHC Ligands. Chemistry \textendash A European Journal, 25(62), 14223--14229.
Goh, Shermin S, & Champagne, Pier, & Guduguntla, Sureshbabu, & Kikuchi, Takashi, & Fujita, Makoto, & Houk, Kendall N, & Feringa, Ben L (2018). Stereospecific Ring Contraction of Bromocycloheptenes through Dyotropic Rearrangements via Nonclassical Carbocation--Anion Pairs. Journal of the American Chemical Society, 140(15), 4986--4990.
Maji, Rajat, & Champagne, Pier, & Houk, Kendall N, & Wheeler, Steven E (2017). Activation Mode and Origin of Selectivity in Chiral Phosphoric Acid-Catalyzed Oxacycle Formation by Intramolecular Oxetane Desymmetrizations. ACS Catalysis, 7(10), 7332--7339.
Champagne, Pier, & Houk, Kendall N (2016). Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations. Journal of the American Chemical Society, 138(38), 12356--12359.
Champagne, Pier, & Desroches, Justine, & Hamel, Jean-Denys, & Vandamme, Mathilde, & Paquin, Jean-Francois (2015). Monofluorination of organic compounds: 10 years of innovation. Chemical reviews, 115(17), 9073--9174.
Champagne, Pier, & Desroches, Justine, & Paquin, Jean-Fran\ccois, (2015). Organic fluorine as a hydrogen-bond acceptor: Recent examples and applications. Synthesis, 47(03), 306--322.
Champagne, Pier, & Benhassine, Yasmine, & Desroches, Justine, & Paquin, Jean-Fran\ccois, (2014). Friedel--Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding. Angewandte Chemie International Edition, 53(50), 13835--13839.
Ribéraud, Maxime, & Porte, Karine, & Chevalier, Arnaud, & Madegard, Léa, & Rachet, Aurélie, & Delaunay-Moisan, Agnès, & Vinchon, Florian, & Thuéry, Pierre, & Chiappetta, Giovanni, & Champagne, Pier, & Pieters, Grégory, & Audisio, Davide, & Taran, Frédéric (2023). Fast and Bioorthogonal Release of Isocyanates in Living Cells from Iminosydnones and Cycloalkynes. Journal of the American Chemical Society, 145(4), 2219-2229.
Sharma, Jyoti, & Champagne, Pier Alexandre (2022). Benchmark of density functional theory methods for the study of organic polysulfides. Journal of Computational Chemistry, 43(32), 2131-2138.
Birepinte, Mélodie, & Champagne, Pier Alexandre, & Paquin, Jean-François (2022). Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes. Angewandte Chemie International Edition, 61(1), e202112575.
Feng, Minghao, & Madegard, Léa, & Riomet, Margaux, & Louis, Manon, & Champagne, Pier, & Pieters, Grégory, & Audisio, Davide, & Taran, Frédéric (2022). Selective chlorination of iminosydnones for fast release of amide, sulfonamide and urea-containing drugs. Chemical Communications, 58(61), 8500--8503.
Buttard, Floris, & Champagne, Pier (2022). Binding Modes and Origins of Enantioselectivity in the Phase-Transfer-Catalyzed Conjugate Cyanation of $\beta$-Trifluoromethylated Chalcones. ACS Catalysis, 12(14), 8185--8194.
Nnamdi, Fred U, & Diner, Colin, & Champagne, Pier, & Organ, Michael G (2021). Experimental and Computational Study on the Anti-Markovnikov Hydrofunctionalization of Olefins Using Glycine-Extended AQ-Auxiliaries.. Chemistry - A European Journal, 27(11), 3855--3860.
Yen-Pon, Expédite, & Buttard, Floris, & Fr\'ed\'eric, Lucas, , & Thuéry, Pierre, & Taran, Frédéric, & Pieters, Grégory, & Champagne, Pier, & Audisio, Davide (2021). Heterohelicenes through 1, 3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal. JACS Au, 1, 807-818.
Champagne, Pier (2021). Identifying the true origins of selectivity in chiral phosphoric acid catalyzed N-acyl-azetidine desymmetrizations. Chemical Science, 12, 15662-15672.
Buttard, Floris, & Sharma, Jyoti, & Champagne, Pier (2021). Recent advances in the stereoselective synthesis of acyclic all-carbon tetrasubstituted alkenes. Chemical Communications, 57, 4071-4088.
Liu, Chengyuan, & Wang, Qi, & Hivick, Brian E, & Ai, Yongling, & Champagne, Pier, & Pan, Yang, & Chen, Hao (2020). Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry. Analytical Chemistry, 92(23), 15291--15296.
Houle, Camille, & Savoie, Paul R, & Davies, Clotilde, & Jardel, Damien, & Champagne, Pier, & Bibal, Brigitte, & Paquin, Jean-Fran\ccois, (2020). Thiourea-catalyzed C--F Bond Activation: Amination of Benzylic Fluorides. Chemistry--A European Journal, 26(46), 10620--10625.
Sinha, Narayan, & Champagne, Pier, & Rodriguez, Michael J, & Lu, Yu, & Kopach, Michael E, & Mitchell, David, & Organ, Michael G (2019). One-Pot Sequential Kumada--Tamao--Corriu Couplings of (Hetero) Aryl Polyhalides in the Presence of Grignard-Sensitive Functional Groups Using Pd-PEPPSI-IPentCl. Chemistry--A European Journal, 25(26), 6508--6512.
Yen-Pon, Exp\'edite, , & Champagne, Pier, & Plougastel, Lucie, & Gabillet, Sandra, & Thu\'ery, Pierre, , & Johnson, Mizuki, & Muller, Gilles, & Pieters, Gr\'egory, , & Taran, Fr\'ed\'eric, , & Houk, Kendall N, & others, (2019). Sydnone-Based Approach to Heterohelicenes through 1, 3-Dipolar-Cycloadditions. Journal of the American Chemical Society, 141(4), 1435--1440.
Lombardi, Christopher, & Rucker, Richard P., & Froese, Robert D. J., & Sharif, Sepideh, & Champagne, Pier, & Organ, Michael G. (2019). Rate and Computational Studies for Pd-NHC-Catalyzed Amination with Primary Alkylamines and Secondary Anilines: Rationalizing Selectivity for Monoarylation versus Diarylation with NHC Ligands. Chemistry \textendash A European Journal, 25(62), 14223--14229.
Goh, Shermin S, & Champagne, Pier, & Guduguntla, Sureshbabu, & Kikuchi, Takashi, & Fujita, Makoto, & Houk, Kendall N, & Feringa, Ben L (2018). Stereospecific Ring Contraction of Bromocycloheptenes through Dyotropic Rearrangements via Nonclassical Carbocation--Anion Pairs. Journal of the American Chemical Society, 140(15), 4986--4990.
Maji, Rajat, & Champagne, Pier, & Houk, Kendall N, & Wheeler, Steven E (2017). Activation Mode and Origin of Selectivity in Chiral Phosphoric Acid-Catalyzed Oxacycle Formation by Intramolecular Oxetane Desymmetrizations. ACS Catalysis, 7(10), 7332--7339.
Champagne, Pier, & Houk, Kendall N (2016). Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations. Journal of the American Chemical Society, 138(38), 12356--12359.
Champagne, Pier, & Desroches, Justine, & Hamel, Jean-Denys, & Vandamme, Mathilde, & Paquin, Jean-Francois (2015). Monofluorination of organic compounds: 10 years of innovation. Chemical reviews, 115(17), 9073--9174.
Champagne, Pier, & Desroches, Justine, & Paquin, Jean-Fran\ccois, (2015). Organic fluorine as a hydrogen-bond acceptor: Recent examples and applications. Synthesis, 47(03), 306--322.
Champagne, Pier, & Benhassine, Yasmine, & Desroches, Justine, & Paquin, Jean-Fran\ccois, (2014). Friedel--Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding. Angewandte Chemie International Edition, 53(50), 13835--13839.
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