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Stable CAAC-based Ruthenium Complexes for Dynamic Olefin Metathesis Under Mild Conditions

preprint
submitted on 18.01.2021, 19:15 and posted on 20.01.2021, 05:18 by Oleksandr Kravchenko, Brian J.J. Timmer, Maurice Biedermann, Andrew Kentaro Inge, Olof Ramstrom

A series of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbene (CAAC) ligands of varying size and steric demand has been synthesized and evaluated in ring-closing-, self-, and cross-metathesis reactions at room temperature. The catalysts were also probed for potential applications in dynamic covalent chemistry. The majority of the catalysts showed high stability, and remained active in the reaction mixtures for several days, including in methanol-based solutions. Higher temperatures could be used to control the reactivity towards sterically challenging substrates, enabling formation of tetrasubstituted olefins. The CAAC complexes exhibited remarkable functional group tolerance towards heteroaromatic and nucleophilic additives, making them potentially useful in the screening of biologically active compounds.

History

Email Address of Submitting Author

olof_ramstrom@uml.edu

Institution

University of Massachusetts Lowell

Country

United States

ORCID For Submitting Author

0000-0002-1533-6514

Declaration of Conflict of Interest

No conflict of interest

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