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Issue 47, 2016
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Silver-mediated direct trifluoromethoxylation of α-diazo esters via the OCF3 anion

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Abstract

Silver-mediated direct trifluoromethoxylation of α-diazo esters and ketosteroid was disclosed. The reactions of alkyl α-diazo arylacetates with AgOCF3 or CF3SO2OCF3/AgF at −30 to 10 °C under a N2 atmosphere provided α-trifluoromethoxyl arylacetates in up to 90% yield, while alkyl α-diazo vinylacetates reacting with CF3SO2OCF3/AgF or AgOCF3 afforded γ-trifluoromethoxyl α,β-unsaturated esters in up to 94% yield. The α-diazo ketosteroid was also trifluoromethoxylated under the standard reaction conditions. This protocol allows for an effective and convenient access to a large number of synthetic building blocks, which are promising in the development of new functional OCF3-molecules.

Graphical abstract: Silver-mediated direct trifluoromethoxylation of α-diazo esters via the −OCF3 anion

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Supplementary files

Article information


Submitted
12 Apr 2016
Accepted
20 Apr 2016
First published
21 Apr 2016

Chem. Commun., 2016,52, 7458-7461
Article type
Communication

Silver-mediated direct trifluoromethoxylation of α-diazo esters via the OCF3 anion

G. Zha, J. Han, X. Hu, H. Qin, W. Fang and C. Zhang, Chem. Commun., 2016, 52, 7458
DOI: 10.1039/C6CC03040H

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