Seminar
calendar 13/09/2024
clock 11:00

Branched Dienes as a Platform for Selective Catalysis

In addition to being a common structural element in many natural products and biologically active molecules, conjugated dienes serve as building blocks in the synthesis of a wide range of compounds, from fine chemicals to functional polymers. Because the inherent reactivity of dienes is influenced by the nature, number and relative position of their substituents, they also provide a particularly modular and versatile platform for the discovery and development of catalytic methods that streamline access to more complex, polyfunctional small molecules.1,2 More specifically, beyond any reactivity considerations, transition metal-catalyzed functionalization of dienes is generally confronted with the difficulty of exerting excellent chemo-, regio-, diastereo- and enantio-control. In this presentation, we will disclose catalytic methods for the selective functionalization of branched dienes and discuss relevant mechanistic aspects.

[1] (a) Thirsk, C.; Whiting, A. Polyene natural products. J. Chem. Soc. Perkin Trans. 2002, 1, 999; (b) Herrmann, N.; Vogelsang, D.; Behr, A.; Seidensticker, T. Homogeneously Catalyzed 1,3-Diene Functionalization−A Success Story from Laboratory to Miniplant Scale. ChemCatChem 2018, 10, 5342. (c) Qi, Y.; Liu, Z.; Liu, S.; Cui, L.; Dai, Q.; He, J.; Dong, W.; Bai, C. Catalysts 2019, 9, 97.

[2] (a) Adamson. N. J.; Malcolmson, S. J. Catalytic Enantio- and Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes. ACS Catal. 2020, 10, 1060. (b) Perry, G. J. P.; Jia, T.; Procter, D. J. Copper-Catalyzed Functionalization of 1,3-Dienes: Hydrofunctionalization, Borofunctionalization, and Difunctionalization. ACS Catal. 2020, 10, 1485.

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