Impact of the Carbene Derivative Charge on the Decomposition Rates of Hoveyda–Grubbs-like Metathesis Catalysts

Hoveyda–Grubbs
metathesis catalysts undergo a relatively
fast decomposition in the presence of olefins. Using a computational
density functional theory approach, we show that positively charged
derivatives of N-heterocyclic carbenes have little impact on the degradation/deactivation
rates of such catalysts with respect to neutral carbenes. On the other
hand, the hypothetical anionic Hoveyda–Grubbs-like catalysts
are predicted to less likely undergo degradation in the presence of
the olefin, while being as active as standard, neutral Hoveyda–Grubbs
catalysts.