Iridium-promoted conversion of terminal epoxides to primary alcohols under acidic conditions using hydrogen

A strategy for the conversion of terminal epoxides to primary alcohols is presented. The reaction uses hydrogen as the only stoichiometric reagent and is promoted by an iridium precatalyst under acidic conditions. Selectivity for the formation of a terminal alcohol over an internal alcohol is observ...

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Bibliographic Details
Published in:Catalysis science & technology 2019, Vol.9 (12), p.32-322
Main Authors: Rainsberry, Alena N, Sage, Jarrod G, Scheuermann, Margaret L
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aromatic compounds
Conversion
Iridium
Reagents
Selectivity
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Summary:A strategy for the conversion of terminal epoxides to primary alcohols is presented. The reaction uses hydrogen as the only stoichiometric reagent and is promoted by an iridium precatalyst under acidic conditions. Selectivity for the formation of a terminal alcohol over an internal alcohol is observed for both alkyl- and aryl-substituted terminal epoxides in isolated yields of up to 50% and 72% respectively. Terminal aliphatic epoxides can be converted to primary alcohols rather than the more commonly formed secondary alcohols.
ISSN:2044-4753
2044-4761
DOI:10.1039/c9cy00791a