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Room‐Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity

Teng Wei Ng, Gang Liao, Kai Kiat Lau, Hui‐Jie Pan, Yu Zhao

2020Angewandte Chemie International Edition108 citationsDOI

Abstract

We report herein an unprecedented highly efficient Guerbet-type reaction at room temperature (catalytic TON up to >6000). This β-alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher-order secondary alcohols in an economical, redox-neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee. In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.

Topics & Concepts

CatalysisChemistryCatalytic efficiencyCombinatorial chemistryChemical engineeringMaterials scienceOrganic chemistryEngineeringAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisChemical Synthesis and Analysis
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