AI Article Synopsis
- Selective hydrogenation of epoxides is a promising but challenging method for producing alcohols.
- This study demonstrates a new electrochemical process to hydrogenate epoxides using electrons and protons without metal catalysts, yielding various alcohols.
- The regioselectivity during this process is influenced by factors like the stability of created benzyl radicals in aryl-substituted epoxides and the kinetics of the reaction for alkyl-substituted epoxides.
Article Abstract
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.
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| http://dx.doi.org/10.1021/jacs.1c11791 | DOI Listing |
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