C&CB Department Seminar – Sophie Rousseaux (University of Toronto)
Oct 21, 2021
1:30PM to 2:30PM
Date(s) - 21/10/2021
1:30 pm - 2:30 pm
Title: New Strategies for the Synthesis of SmallRings and Nitriles
Date: Thursday, October 21, 2021
Zoom : link available from firstname.lastname@example.org
Host: Andrew Osamudiamen (Brook Group)
Abstract: Research in the Rousseaux group focuses on the development of new syntheticmethods to selectively break and/or form new bonds in organic molecules, namelythrough the use of Ni catalysis. Our approach to method development reliesheavily on mechanistic studies to design improved catalysts and reactionconditions, ultimately leading to broader reaction scopes and the discovery ofnew reactivity. In this presentation, I will describe our efforts to developnew synthetic methods in two areas.
In the first part of this talk,I will discuss our recent work on the functionalization of cyclopropanolderivatives. Reactions involving electrophilic metal homoenolates1 willbe presented as well as Ni-catalyzed cross-couplings of cyclopropanols.2I will also present recent work on the synthesis of cyclobutanols from readilyavailable starting materials.3
In part two, I will describe our current efforts in developing new syntheticmethods for the preparation of nitrile-containing building blocks that useinexpensive and less toxic nitrile-transfer reagents.4,5 Our work onthe development of Ni-catalyzed reductive transnitrilation reactions will alsobe presented.6
1.(a) Mills, L. R.; Barrera Arbelaez, L. M.; Rousseaux, S. A. L. J. Am. Chem.Soc. 2017, 139, 11357–11360; (b) West, M. S.; Mills, L. R.;McDonald, T. R.; Lee, J. B.; Ensan, D.; Rousseaux, S. A. L. Org. Lett. 2019,21, 8409–8413.
2.(a) Mills, L. R.; Zhou, C.; Fung, E. Org. Lett. 2019, 21,8805–8809; (b) Mills, L. R.; Monteith, J. J.; Rousseaux, S. A. L. J. Am.Chem. Soc. 2020, 142, 13246–13254; (c) Mills, L. R.;Monteith, J. J.; Rousseaux, S. A. L. Chem. Commun. 2020, 56,12538–12541.
3.McDonald, T. R.; Rousseaux, S. A. L. Unpublished.
4.Alazet, S.; West, M. S.; Patel, P.; Rousseaux, S. A. L. Angew. Chem. Int.Ed. 2019, 58, 10300-10304; Mills, L. R.; Rousseaux, S. A. L. Tetrahedron2019, 75, 4298-4306.
5.Mills, L. R.; Edjoc, R. K.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2021, 143, 10422–10428.
6.(a) Mills, L. R.; Graham, J.; Patel, P.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2019, 141,19257–19262; (b) Patel, P.; Palermo, A.; Rousseaux, S. A. L. Manuscript inPreparation.