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Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative Cross-Coupling of Alcohols

Dipanjan Bhattacharyya, Bikash Kumar Sarmah, Sekhar Nandi, Hemant Kumar Srivastava, Animesh Das

2021Organic Letters67 citationsDOI

Abstract

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.

Topics & Concepts

ChemistryAlkylationCatalysisPrimary (astronomy)PhosphinePincer movementOrganic chemistryRutheniumCombinatorial chemistryKetonePhysicsAstronomyAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisCarbon dioxide utilization in catalysis
Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative Cross-Coupling of Alcohols | Litcius