Dr. Sophie Rousseaux presents the McRae Lecture

New Developments in Ni-Catalyzed Transnitrilation

Sophie Rousseaux*^a

^aDepartment of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada

Email: sophie.rousseaux@utoronto.ca

Accessing medicinally relevant small molecules in a more efficient and/or safer manner continues to drive important discoveries in synthetic organic chemistry. My group is particularly interested in the development of new Ni-catalyzed processes to address these challenges and the use of readily available building blocks to access complex small molecules.

The preparation of nitrile-containing organic molecules has garnered considerable attention from the community for over a century due to their prevalence in pharmaceuticals and their versatility as synthetic intermediates. In this field, the use of toxic cyanide salts (and their equivalents) or HCN as a source of nitrile to forge C–CN bonds remains a problem.  To address this challenge, my group is developing new synthetic methods that use inexpensive and less toxic nitrile-transfer reagents for the synthesis of these compounds. We have demonstrated that valuable nitrile-containing building blocks can be prepared based on the concept of nitrile-transfer (or “transnitrilation”).^1,2 This presentation will highlight our contributions to this field, with a particular focus on the development of Ni-catalyzed methods for the synthesis of nitriles.²

References
[1] a) Alazet, S.; West, M. S.; Patel, P.; Rousseaux, S. A. L. Angew. Chem. Int. Ed. 2019, 58, 10300–10304; b) Mills, L. R.; Rousseaux, S. A. L. Tetrahedron 2019, 75, 4298–4306.

[2] a) Mills, L. R.; Graham, J.; Patel, P.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2019, 141, 19257–19262; b) Mills, L. R.; Edjoc, R. K.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2021, 143, 10422–10428; (c) Palermo, A. F.; Chiu, B. S. Y.; Patel, P.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2023, 145, 24981–24989.