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Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

Masaki Kobayashi, Satoshi Itoh, Keisuke Yoshimura, Yuya Tsukamoto, Yasushi Obora

2020The Journal of Organic Chemistry23 citationsDOI

Abstract

(where Cp* = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.

Topics & Concepts

ChemistryAlcoholCatalysisReagentPrimary (astronomy)EthanolAlkylIridiumDeuteriumPrimary alcoholOrganic chemistryHydrogenCombinatorial chemistryQuantum mechanicsPhysicsAstronomyAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisChemical Reactions and Isotopes
Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction | Litcius