Regioselective ring-opening of epoxides towards Markovnikov alcohols: a metal-free catalytic approach using abnormal N-heterocyclic carbene

Herein we report the first metal-free regioselective Markovnikov ring-opening of epoxides (selectivity up to 99%) using an abnormal N-heterocyclic carbene (aNHC) to yield secondary alcohols. DFT calculations and X-ray crystallography suggest that the Markovnikov selectivity originates from the high nucleophilicity and steric factors associated with the aNHC.

Automated summary

This study reports the metal-free regioselective Markovnikov ring-opening of epoxides using an abnormal N-heterocyclic carbene (aNHC) to yield secondary alcohols with up to 99% selectivity. DFT calculations and X-ray crystallography suggest that the Markovnikov selectivity is attributed to the high nucleophilicity and steric factors of the aNHC.