Carbonyl-olefin metathesis (COM) is a powerful tool allowing synthetic chemists to create new C=C bonds for further functionalization. We have previously demonstrated that, at the beginning of the reaction, the primary COM catalytic cycle prevails. However, as the reaction progresses and more carbonyl byproduct accumulates, the rate slows. This rate decrease is a result of carbonyl byproduct sequestering the FeCl<sub>3</sub> catalyst, forming highly ligated Fe(III)-carbonyl species in solution. This highly ligated Fe(III)-carbonyl species will then result in the creation of a secondary catalytic cycle which will dominate further into the reaction. Preventing this byproduct inhibition may be the key to unlocking previously unsuccessful COM substrates and lowering catalyst loading. Synthetic chemists have shown that certain additives impact the rate of FeCl<sub>3</sub>-catalyzed COM and Prins reactions. Herein, we report an investigation into the impact of additives on the mechanism of carbonyl-olefin metathesis.

Impact of additives on the rate of carbonyl-olefin metathesis

ACS Spring 2022

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