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Epoxide Electroreduction
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DOI：10.1021/jacs.1c11791.png)
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摘要
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.
Keyword:
ANTI-MARKOVNIKOV ALCOHOLS
RADICAL REDUCTION
METAL-REDUCTION
TITANOCENE
ELECTROCHEMISTRY
HYDROGENATION
MECHANISM
ELECTROSYNTHESIS
STEREOCHEMISTRY
HETEROCYCLES
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期刊
IF:
15.6
论文数:
20.1W
被引数:
60.2W
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引用论文
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