posted on 2021-12-29, 09:04authored byCheng Huang, Wan Ma, Xuelian Zheng, Minghao Xu, Xiaotian Qi, Qingquan Lu
Selective
hydrogenation of epoxides would be a direct and powerful
approach for alcohol synthesis, but it has proven to be elusive. Here,
electrochemically epoxide hydrogenation using electrons and protons
as reductants is reported. A wide range of primary, secondary, and
tertiary alcohols can be achieved through selective Markovnikov or
anti-Markovnikov ring opening in the absence of transition metals.
Mechanistic investigations revealed that the regioselectivity is controlled
by the thermodynamic stabilities of the in situ generated benzyl radicals
for aryl-substituted epoxides and the kinetic tendency for Markovnikov
selective ring opening for alkyl-substituted epoxides.