Olefin metathesis is one of the most powerful transformations in organic synthesis. A variety of catalysts allow for the formation of either kinetic or thermodynamic products. Ability to establish equilibrium between alkenes would enable applications of olefin metathesis in dynamic covalent chemistry. However, even stable NHC-bearing catalysts suffer from poor stability and reduced functional group tolerance, limiting possible applications in dynamic chemistry. Recently developed CAAC-bearing catalysts exhibited superior performance in the ethenolysis reaction, which is attributed to the increased stability of catalytic intermediates [1].<br/><br/>In the present study, we synthesized a series of CAAC-based ruthenium complexes with varying stability/activity balance [2]. These complexes were evaluated as catalysts in benchmark olefin metathesis reactions and proved able to generate simple dynamic systems. Finally, in order to assess tolerance towards functionalized substrates, one of the catalysts was subjected to additive screening.<br/><br/>

Stable CAAC-based complexes in dynamic olefin metathesis

256th National Meeting (2018)

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