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Presented By: Department of Chemistry

Gomberg Lecture - Carbenes as Powerful Transition-Metal Surrogates

Guy Bertrand (UC San Diego)

Since the discovery at the beginning of the XXth century of a stable radical, many species that do not obey the octet rule have been isolated. The availability of these stable versions has led to a variety of applications. This statement is well supported by the example of stable carbenes, with only six-valence electrons, which have become among the most powerful tools in chemistry.
Our recent results dealing with the development of catalytic processes promoted by carbenes, which are genuine organic compounds, will be discussed.1-4 They could address the major drawbacks of current transition metal catalysis technology that are the excessive cost of metal complexes (metal + ligands) and in many cases the toxicity of the metal.
To push the boundaries further, we wish to undress carbon atoms even more. As an illustration we will discuss our results dealing with a dicoordinate carbodication.5,6

1 J. L. Peltier, E. Tomas-Mendivil, D. R. Tolentino, M. M. Hansmann, R. Jazzar, G. Bertrand, J. Am. Chem. Soc. 2020, 142, 18336-18340.
2 W. Liu, A. Vianna, Z. Zhang, S. Huang, L. Huang, M. Melaimi, G. Bertrand, X. Yan. Chem. Catalysis 2021, 1, 196-206.
3 Z. Zhang, S. Huang, C.-Y. Li, L.-L. Zhao, W. Liu, M. Melaimi, G. Bertrand, X. Yan. Chem Catalysis 2022, 2, 3517-3527.
4 C. Liu, Z. Zhang, L.-L. Zhao, G. Bertrand, X. Yan. Angew. Chem. Int. Ed. 2023, e202303478.
5 Y. K. Loh, M. Melaimi, D. Munz, G. Bertrand. J. Am. Chem. Soc. 2023, 145, 2064-2069.
6 Y. K. Loh, M. Melaimi, M. Gembicky, D. Munz, G. Bertrand. Nature 2023, 623, 66-70.

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