An air-stable cationic iridium hydride as a highly active and general catalyst for the isomerization of terminal epoxides

We describe the use of an air-stable iridium hydride catalyst for the isomerization of terminal epoxides into aldehydes with perfect regioselectivity. The system operates at low loadings of catalyst (0.5 mol%), is highly practical, scalable, and tolerates functional groups that would not be compatib...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 73; pp. 10592 - 10595
Main Authors Humbert, Nicolas, Vyas, Devendra J., Besnard, Celine, Mazet, Clement
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.09.2014
Subjects
Catalysts
Cationic
Chemistry
Chemistry, Multidisciplinary
Compatibility
Hydrides
Iridium
Isomerization
Lewis acid
Physical Sciences
Science & Technology
Terminals
PRIMARY ALLYLIC ALCOHOLS
COMPLEX
ASYMMETRIC ISOMERIZATION
KINETIC RESOLUTION
SUBSTITUTED BENZYLIC ALDEHYDES
MEINWALD REARRANGEMENT REACTIONS
SELECTIVE SYNTHESIS
STEREOSELECTIVE REARRANGEMENT
DERIVATIVES
PROMOTED REARRANGEMENT
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Summary:We describe the use of an air-stable iridium hydride catalyst for the isomerization of terminal epoxides into aldehydes with perfect regioselectivity. The system operates at low loadings of catalyst (0.5 mol%), is highly practical, scalable, and tolerates functional groups that would not be compatible with Lewis acids typically used in stoichiometric amounts. Evidence for a rare hydride mechanism are provided.
Bibliography:Swiss National Science Foundation (SNF)
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc05260a