Palladium-Catalyzed Carbon-Heteroatom Bond-Forming Reactions for the Functionalization of Molecules Big and Small
Stephen L. Buchwald
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA USA
Abstract:
Cross-coupling methodology is an indispensable part of the everyday repertoire of synthetic organic chemists. bonds1,2); a mechanistic scheme for this transformation is shown below. This methodology has been widely utilized throughout academia and industry.
This lecture will include:
- An introduction to palladium-catalyzed carbon-heteroatom bond-forming reactions including an historical overview.
- A description of ligand and precatalyst development employing biarylphosphines.
- Applications of these catalysts to the preparation of compounds of interest to medicinal chemists.
- Examples of the use of Pd complexes for the selective functionalization of large molecules.
- If time permits, some of our recent development of Cu catalysts for C-heteroatom bond formation.
References:
1. Ruiz-Castillo, P. and Buchwald, S.L. Chem. Rev. 2016, 116, 12564-12649.
2. Ingoglia, B.T.: Wagen, C.C. and Buchwald, S.L. Tet., 2019, 75, 4199–4211.
3. Reichert, E.C.; Feng, K.; Sather, A.C. and Buchwald, S.L. "Pd-Catalyzed Amination of Base-Sensitive Five-Membered Heteroaryl Halides with Aliphatic Amines." DOI 10.1021/jacs.2c13520.
4. Vinogradova, E.V., Zhang, C.; Spokoyny, A.M.; Pentelute, Bradley L. and Buchwald, S.L. Nature, 2015,
526, 687-691.
5. Kim, S.-T.; Strauss, M.J.; Cabré, A. and Buchwald, S.L. “Room Temperature Cu-Catalyzed
Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design.” J. Am. Chem. Soc.
2023, 145, 6966-6975.
This lecture also represents the 1st faculty colloquium of the winter term: ChemKolloquium (univie.ac.at)
