Wed, 08 Nov 2023
Seminar Series

Dr. Sophie Rousseaux

University of Toronto

New Strategies for the Synthesis of Small Rings and Nitrile Derivatives

Wednesday, November 08, 2023
SSB 7172 @ 3:30 p.m.

Host: Dr. Robert Britton



Research in the Rousseaux group focuses on the development of new synthetic methods to selectively break and/or form new bonds in organic molecules, namely through the use of Ni catalysis. Our approach to method development relies on mechanistic studies to design improved catalysts and reaction conditions, ultimately leading to broader reaction scopes and the discovery of new reactivity. In this presentation, I will describe our efforts to develop new synthetic methods in two areas.

In the first part of this talk, I will discuss our recent work on the synthesis and functionalization of cyclopropanols and cyclobutanols. Reactions involving electrophilic metal homoenolates1 will be presented as well as Ni-catalyzed cross-couplings of cyclopropanols.2 In part two, I will describe our current efforts in developing new synthetic methods for the preparation of nitrile-containing building blocks that use inexpensive and less toxic nitriletransfer reagents.3,4 Our work on the development of Ni-catalyzed reductive transnitrilation reactions will also be presented.5

  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. 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. Tetrahedron 2019, 75, 4298-4306.
  4. Mills, L. R.; Edjoc, R. K.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2021, 143, 10422–10428.
  5. Mills, L. R.; Graham, J.; Patel, P.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2019, 141, 19257–19262.