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Iridium-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols: A Route to Access Branched Ketones and Alcohols

Sertaç Genç, Süleyman Gülcemal, Salih Günnaz, Bekır Çetınkaya, Derya Gülcemal

2020The Journal of Organic Chemistry36 citationsDOI

Abstract

Under borrowing hydrogen conditions, NHC–iridium(I) catalyzed the direct or one-pot sequential synthesis of α,α-disubstituted ketones via the alkylation of secondary alcohols with primary alcohols is reported. Notably, the present approach provides a new method for the facile synthesis of α,α-disubstituted ketones and featured with several characteristics, including a broad substrate scope, using easy-to-handle alcohols as starting materials, and performing the reactions under aerobic conditions. Moreover, the selective one-pot formation of β,β-disubstituted alcohols was achieved by the addition of an external hydrogen source to the reaction mixture.

Topics & Concepts

IridiumPrimary (astronomy)AlkylationCatalysisAlcohol oxidationChemistryOrganic chemistryAlcoholKetoneSubstrate (aquarium)HydrogenPrimary alcoholCombinatorial chemistryGeologyPhysicsOceanographyAstronomyAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisOrganoboron and organosilicon chemistry
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