Guest Speaker – Analytical (CHEM 741) – April 18, 2023

Bio
Sophie Rousseaux obtained a B.Sc. in Biopharmaceutical Sciences – Medicinal Chemistry from the University of Ottawa, Canada, in 2007. As an undergraduate student, she worked with Prof. Keith Fagnou on the direct arylation of pyridine N-oxides and decarboxylative ketone aldol reactions. She remained in the Fagnou group for the start of her graduate studies, working on Pd-catalyzed aliphatic C–H bond functionalization reactions. In 2010, she moved to MIT to complete her graduate research with Prof. Stephen L. Buchwald, working on Pd-catalyzed dearomatization reactions.
In 2012, she moved to the University of Oxford to work with Prof. Harry L. Anderson on the self-assembly of porphyrin nanorings as an NSERC postdoctoral fellow and Glasstone Research Fellow. During her time at Oxford, Sophie also held a Junior Research Fellow at St John’s College (2012–2015) and was a Stipendiary Lecturer in Organic Chemistry at Jesus College (2014).
In July 2015, Sophie returned to Canada to join the Department of Chemistry at the University of Toronto as an Assistant Professor, where she was promoted to Associate Professor in July 2022. She holds a Canada Research Chair (Tier 2) in Organic Chemistry since 2016. Her group’s research interests include organic synthesis, catalysis, and organometallic chemistry, with a particular focus on the synthesis of small rings and nitrile-containing molecules.
Selected recent awards include the McLean Award (2022), the University of Toronto School of Graduate Studies Early Career Supervision Award (2022), the Organic Letters Outstanding Publication of the Year Lectureship (2022), a Sloan Research Fellowship (2021), an Ontario Early Researcher Award (2021), and the Dorothy Shoichet Women Faculty Science Award of Excellence (2020).

Abstract
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. <sup>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.</sup>