Diazoalkanes and Diazirines
Andrea Lapi is pleased to invite to the seminar:
Diazoalkanes and Diazirines: Useful Synthetic Reagents in Si–H Insertion and Cycloaddition Reactions
Thierry Ollevier
Département de chimie, Université Laval Québec, Canada
The seminar will be held in Parravano hall, first floor - S. Cannizzaro building CU014, on Tuesday 6th June at 2.30 pm.
It can be followed in streaming on Google meet: uoy-ybay-efm.
Abstract
Recent synthetic methods for the synthesis of diazoalkanes will be first disclosed. [1] The insertion reaction of diazo compounds into X–H bonds will be presented using copper and iron catalysis. A C2-symmetric copper(I) diimine complex enables the asymmetric insertion reaction of 1-aryl-2,2,2-trifluoro-1-diazoethanes to give enantioenriched (1-aryl-2,2,2- trifluoroethyl)silanes with enantioselectivities up to 96% ee. [2] An efficient synthesis of 3- trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction of alkynes with photolytically-generated carbenes from diazirines will be disclosed. This reaction is performed in continuous flow using readily available LEDs in mild reaction conditions. This new and efficient method describes the synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes with yields up to 97%, achieved in continuous flow with 5 min residence time. The cyclopropanation reaction of alkenes with photolytically-generated halocarbenes from halodiazirines is also presented as an effective way to prepare 3-halo-3-arylcyclopropanes in continuous flow. [3]
References
- (a) Tanbouza, N.; Caron, L.; Khoshoei, A.; Ollevier, T. Org. Lett. 2022, 24, 2675. (b) Tanbouza, N.; Petti, A.; Leech, M.; Caron, L.; Walsh, J.; Lam, K.; Ollevier, T. Org. Lett. 2022, 24, 4665
- (a) Ollevier, T.; Carreras, V. ACS Org. Inorg. Au 2022, 2, 83. (b) Carreras, V.; Ollevier, T. J. Org. Chem. 2021, 86, 13160. (c) Carreras, V.; Besnard, C.; Gandon, V; Ollevier, T. Org. Lett. 2019, 21, 9094
- (a) Tanbouza, N.; Carreras, V.; Ollevier, T. Org. Lett. 2021, 23, 5420. (b) To, H.-M.; Malets, O.; Mazur, M.; Mykhailenko, O.; Kompaniiets, O.; Ollevier, T. Synthesis 2023, 55, 263.
Biographic sketch
Thierry Ollevier was born in Brussels and obtained his B.Sc. (1991) and Ph.D. (1997) at the Université of Namur (Belgium), and was post doctorate fellow at the Université catholique de Louvain (Belgium), under I. E. Markó (1997), NATO postdoctorate fellow at Stanford University under B. M. Trost (1998–2000), then post doctorate fellow at the Université de Montréal under A. B. Charette (2000–2001). After an Assistant Professor appointment (2001) at Université Laval (Québec, Canada), he became Associate (2006) and is currently Full Professor. Current research in his group aims at designing novel catalysts, developing catalytic reactions and applying these methods to chemical synthesis. He is active in the areas of iron catalysis, ligand design, asymmetric catalysis, fluorine chemistry, diazo and diazirine chemistry, flow chemistry, and bismuth chemistry. He has published more than 85 papers and 35 encyclopedia articles and book chapters.
He has served as an Associate Editor of RSC Advances from 2015 to 2022 and was admitted as a Fellow of the Royal Society of Chemistry (2016). After 5 years served as Advisory Board member of SynOpen, he has been appointed as Editor-in-Chief of SynOpen in 2023.
Prizes and honors
- Fellow of the Royal Society of Chemistry (UK) (2015–2022)
- “Professor of the Month” awarded by Silicycle, Québec, February 2014
- “Best Young Presenter Prize” awarded by the Australian Journal of Chemistry at the Eurasia12 meeting, Corfu, April 2012
- Professeur étoile (Teaching prize based on the students’ evaluations, Faculté des sciences et de génie, Université Laval, 2022-2017, 2014, 2013, 2011, 2010, 2004)
- Highlighted articles: Synfacts (9), ChemInform (14), journal covers (6)
- Member of the Commission de terminologie et de néologie de la chimie et des matériaux (Ministère de l’Économie, des Finances et de l’Industrie, Paris) (2010–)
- Prix Stas (Prize from the Belgian Royal Academy, 1997)
Publications and Conferences on Invitation
- 116 Publications (84 research articles, 30 encyclopedia articles, 2 conference proceedings)
- 1 Edited book, 4 book chapters, 1 patent
- 2573 Citations, h factor = 30 (Web of Science, 15 May 2023)
- 110 Conferences on invitation (scientific meetings: 21, univ. & industr. conf.: 89)