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Pier Champagne

Champagne, Pier Alexandre
Assistant Professor, chemistry and environmental
354 tiernan

I am an organic chemist with interests ranging from organic methodology development, to physical organic chemistry and computational organic chemistry. My research focuses on combining experimental and computational tools to develop new chemical reactions of interest, understand the mechanisms of organic reactions, and predict improvements to reported reactions through catalyst engineering or modification of reaction conditions.

Education

  • Ph.D. Organic Chemistry (honors), 2015, Université Laval, Canada
  • B.Sc. Chemistry, 2010, Université Laval, Canada

Professional Experience

  • Postdoctoral researcher, 2017-2018, Department of Chemistry and Biomolecular Sciences, University of Ottawa, Canada
  • FRQNT Postdoctoral fellow, 2015-2017, Department of Chemistry and Biochemistry, University of California, Los Angeles
  • Lecturer, 2013, Département de chimie, Université Laval, Canada

Scholarships and awards

  • Quebec Research Fund – Nature and Technologies (FRQNT) postdoctoral research fellowship, 2015-2017.
  • Honor Board of the Graduate Studies Faculty (excellent doctoral thesis), Université Laval, 2015.
  • Award of excellence for the doctoral seminar, Université Laval, 2015.
  • Natural Sciences and Engineering Research Council of Canada (NSERC) Alexander-Graham-Bell 3rd cycle Canada Graduate Scholarship (CGS D3), 2012-2015.
  • NSERC Alexander-Graham-Bell 2nd cycle Canada Graduate Scholarship (CGS M), 2010.
  • FRQNT master’s research scholarship (B1), 2010.
  • NSERC Undergraduate Student Research Award (USRA), 2008.

Website

http://centers.njit.edu/pachampagne/

Synthesis of complex organoboron building blocks using 1,2-metallate rearrangements

About 40% of all C–C bond-forming reactions in pharmaceutical research use an organoboron compound, mainly by Pd-catalyzed Suzuki-Miyaura cross-couplings of boronic acids or esters. Therefore, it is clear novel reactions to synthesize more complex organoboron building blocks would find immediate use in medicinal chemistry endeavors.

There are two main goals to this project. First, the development of 1,2-metallate rearrangements to obtain stereodefined, tetrasubstituted alkenyl boronic esters. These building blocks can then be engaged in Suzuki couplings to form tetrasubstituted alkenes, which are difficult functional groups to synthesize, yet are known to be crucial in multiple anti-cancer drugs. Second, the development of an organocatalyst system to engage alkenyl boronates in enantioselective 1,2-metallate rearrangements with a wide variety of electrophiles. This will allow access to another important class of organoboron compounds: chiral alkyl boronic esters with multiple contiguous stereocenters, which can then be cross-coupled, or transformed in value-added chiral alcohols and amines.

Computational investigations of organoboron and organocatalyzed transformations

Density functional theory (DFT) calculations are now a widely-used tool to study mechanisms of organic reactions, as they allow investigations of transition structures at a reasonable computational cost.

We plan to use DFT calculations for two main objectives. First to answer questions about the behaviour of organoboron compounds, by computing their mechanisms of reaction and the relevant properties (activation barriers, kinetic isotope effects, substituent effects, etc.). Second, the origins of selectivity in chiral organocatalyzed reactions will be understood. For instance, chiral phosphoric acid catalysis will be investigated for its ability for asymmetric induction is now recognized and used by many research groups. Also, ion-pairing catalysis will be studied, for it is a method of choice for industrial asymmetric synthesis, yet the roles of the catalysts in the enantioselectivity is poorly understood. We hope that these computational studies will allow us to design better catalysts for important transformations.

Selected publications

UCLA

Yen-Pon, E.; Champagne, P. A.; Plougastel, L.; Gabillet, S.; Thuéry, P.; Johnson, M.; Muller, G.; Pieters, G.; Taran, F.; Houk, K. N.; Audisio, D. “Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.” J. Am. Chem. Soc. 2019, dx.doi.org/ 10.1021/jacs.8b11465.

Goh, S. S.; Champagne, P. A.; Guduguntla, S.; Kikuchi, T.; Fujita, M.; Houk, K. N.; Feringa, B. L. “Stereospecific Ring Contraction of Bromocycloheptenes Through Dyotropic Rearrangements via Non-Classical Carbocation-Anion Pairs.” J. Am. Chem. Soc. 2018, 140, 4986-4990.

Champagne, P. A.; Houk, K. N. “Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations.” J. Am. Chem. Soc. 2016, 138, 12356-12359.

Université Laval

Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. “Monofluorination of Organic Compounds: 10 Years of Innovation.” Chem. Rev. 2015, 115, 9073-9174. (Invited contribution)

Champagne, P. A.; Desroches, J.; Paquin, J.-F. “Organic Fluorine as a Hydrogen-Bond Acceptor: Recent Evidence and Applications.” Synthesis 2015, 47, 306-322. (Invited contribution)

Champagne, P. A.; Benhassine, Y.; Desroches, J.; Paquin, J.-F. “Friedel-Crafts Reaction of Benzyl Fluorides: Activation of C–F Bonds as Enabled by Hydrogen-Bonding.” Angew. Chem. Int. Ed. 2014, 53, 13835-13839.

The full list of publications can be found on Google Scholar (link to: https://scholar.google.com/citations?user=e9YHp7IAAAAJ&hl=en).