Issue 1, 2021

Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

Abstract

The epoxidation of olefin as a strategy to protect carbon–carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts.

Graphical abstract: Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

Supplementary files

Article information

Article type
Paper
Submitted
28 8 2020
Accepted
03 11 2020
First published
05 11 2020

Catal. Sci. Technol., 2021,11, 312-318

Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

J. L. Fiorio and L. M. Rossi, Catal. Sci. Technol., 2021, 11, 312 DOI: 10.1039/D0CY01695K

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