An isodesmic approach to metal-free C-H borylation reactions
Department of Chemistry and Biomolecular Sciences 2022-2023 Seminar Series
Nov 30, 2022 — All day
The Department of Chemistry and Biomolecular Sciences hosts guest speakers from the industry, research institutes, other universities, and from our own campus as part of a regular seminar series during the Fall and Winter terms.
Abstract
Our research group has been developing methodologies for the C-H borylation reaction using metal-free catalysis operating through the concept of frustrated Lewis pair (FLP) chemistry.[1-3] While aminoboranes, our first generation of catalysts, could operate the C-H borylation of heteroarenes efficiently, it had several drawbacks, including an intolerance towards many functional groups and contaminants.[4,5] To circumvent these problems, we developed an isodesmic borylation, aka transfer borylation, using arylboronates as borylation agents and 2-mercaptoazoles as catalysts.[6] By avoiding the presence of reactive B-H or B-X moieties throughout the catalytic transformation, we are now able to borylate heteroarenes,[6] alkynes,[7] and electron-rich alkenes that would otherwise undergo side reactions such as hydroboration. This presentation will describe the contributions we made in order to better understand and optimize this transformation.
References
- Stephan, D. J. Am. Chem. Soc. 2015, 137, 10018.
- Fontaine, F.-G; Rochette, É. Acc. Chem. Res. 2018, 51, 454.
- Fontaine, F.-G.; Stephan, D. W. Phi. Trans. R. Soc. A. 2017, 375, 2017004.
- Légaré, M.-A.; Courtemanche, M.-A.; Rochette, É.; Fontaine, F.-G. Science 2015, 349, 513.
- Légaré Lavergne, J.; Jayaraman, A.; Misal-Castro, L.; Rochette, É.; Fontaine, F.-G. J. Am. Chem. Soc. 2017, 139, 14714. [
- Rochette, É.; Desrosiers, V.; Soltani, Y.; Fontaine, F.-G. J. Am. Chem. Soc. 2019, 141, 12305. [7] Desrosiers, V.; Zavaleta Garcia, C.; Fontaine, F.-G. ACS Catal. 2020, 10, 11046.

Frédéric-Georges Fontaine
Département de Chimie, Université Laval, Québec, Canada G1V 0A6
Frédéric-Georges Fontaine obtained his B.Sc. in chemistry at Université de Montréal. He did his Ph.D. in the same establishment under the supervision of Professor Zargarian on the development of nickel catalysts for the dehydropolymerization of hydrosilanes, work for which he got the Governor General Gold Medal. He then undertook an NSERC postdoctoral fellowship with Professor T. Don Tilley at University of California. In 2004, he was appointed professor at Université Laval and became full professor in 2013. He holds a Canada Research Chair in Green Catalysis and Metal-Free chemistry since 2018. His research is focused on metal-free catalysis for the functionalization of C-H bond and CO2 and on the synthesis of materials for green applications. His work, which resulted in over 100 publications including a publication in Science, was considered as one of the top 10 scientific discovery of 2015 according to Quebec Science. He is an alumnus of the Japanese Society for the Promotion of Science (JSPS). He is leading the NSERC CREATE CIRCUIT (Centre for Innovation and Research on Carbon Utilization in Industrial Technologies) since September 2020.
Everyone is welcome.
Contact Info
Prof. Eva Hemmer
Associate Professor, Department of Chemistry and Biomolecular Sciences
Phone: +1-613-562-5800 ext. 1987
Website: www.hemmerlab.com