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A General Regioselective Synthesis of Alcohols by Cobalt‐Catalyzed Hydrogenation of Epoxides

Weiping Liu, Thomas Leischner, Wu Li, Kathrin Junge, Matthias Beller

2020Angewandte Chemie International Edition45 citationsDOIOpen Access PDF

Abstract

Abstract A straightforward methodology for the synthesis of anti‐Markovnikov‐type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf) 2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi‐substituted internal and terminal epoxides, as well as a good functional‐group tolerance. Various natural‐product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate‐to‐excellent yields.

Topics & Concepts

TriphosRegioselectivityChemistryCatalysisCobaltMarkovnikov's ruleOrganic chemistrySubstrate (aquarium)Combinatorial chemistryFunctional groupGeologyPolymerOceanographyAsymmetric Hydrogenation and CatalysisCatalysis for Biomass ConversionCarbon dioxide utilization in catalysis