.png){kind=icon}
Return
Epoxide Electroreduction
.png){kind=icon}
PRE
AI
DOI：10.1021/jacs.1c11791.png)
.png){kind=icon}
.png){kind=icon}
Share.png){kind=icon}
Save
Abstract
En 中文
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.
Keywords:
ANTI-MARKOVNIKOV ALCOHOLS
RADICAL REDUCTION
METAL-REDUCTION
TITANOCENE
ELECTROCHEMISTRY
HYDROGENATION
MECHANISM
ELECTROSYNTHESIS
STEREOCHEMISTRY
HETEROCYCLES
Journal
IF:
15.6
Papers:
20.1W
Citations:
63.3W
Organization
Cited Papers
.png){kind=icon}
ShareSaveShareSaveEmergence of a novel catalytic radical reaction: Titanocene-catalyzed reductive opening of epoxides
PREAI
ShareSave
ShareSaveCatalytic Hydrogen Atom Transfer (HAT) for Sustainable and Diastereoselective Radical Reduction
PREAI
ShareSaveShareSave
View more