Strategies for Selective C–C and C–O Bond Cleavage in Cyclopropanols and Nitriles
Canada Research Chair in Organic Chemistry
Department of Chemistry
University of Toronto
Thursday, January 23, 2019
C2-361 (Reading Room)
Research in the Rousseaux group focuses on the development of new synthetic methods involving reactive organometallic intermediates and/or Ni catalysis. 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 functionalization of cyclopropanol derivatives through selective C–C and C–O bond cleavage. 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 nitrile-transfer reagents.3 Our recent work on the development of Ni-catalyzed reductive transnitrilation reactions will also be presented.4
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 Lett. 2019, 21, 8805–8809; (b) Mills, L. R.; Monteith, J. J.; Rousseaux, S. A. L. Unpublished.
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.; Graham, J.; Patel, P.; Rousseaux, S. A. L. J. Am. Chem. Soc. 2019, 141, 19257–19262.
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