Metal-Catalyzed C–O Cleavage: Mechanistic Understanding and Applications in Chemical Synthesis
Abstract
The mounting global concerns surrounding the sustainable manufacturing of pharmaceuticals, materials, and commodity chemicals have led chemists to pursue greener alternatives to existing processes.1 The development of reactions that directly functionalize naturally derived chemicals such as those originating from lignin and carbon dioxide offer a sustainable solution to this societal need. Cleavage of the C–O linkages commonly encountered in these feedstocks, however, represents a significant barrier due to the typically strong nature of these bonds. This seminar will present mechanistic insights into this class of reactions and blueprints for the development of future reactions.2-3
References:
1. Bullock, R. M.; Chen, J. G.; Gagliardi, L.; Chirik, P. J.; Farha, O. K.; Hendon, C. H.; Jones, C. W.; Keith, J. A.; Klosin, J.; Minteer, S. D.; Morris, R. H.; Radosevich, A. T.; Rauchfuss, T. B.; Strotman, N. A.; Vojvodic, A.; Ward, T. R.; Yang, J. Y.; Surendranath, Y. Using nature's blueprint to expand catalysis with Earth-abundant metals. Science 2020, 369 (6505), eabc3183.
2. Day, C. S.; Somerville, R. J.; Martin, R. Deciphering the dichotomy exerted by Zn(II) in the catalytic sp2 C–O bond functionalization of aryl esters at the molecular level. Nat. Catal. 2021, 4 (2), 124-133.
3. Day, C. S.; Ton, S. J.; Kaussler, C.; Vrønning Hoffmann, D.; Skrydstrup, T. Low Pressure Carbonylation of Benzyl Carbonates and Carbamates for Applications in 13C Isotope Labeling and Catalytic CO2 Reduction. Angew. Chem. Int. Ed. 2023, e202308238.
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