Trifluoroacetic Anhydride-Catalyzed Oxidation of Isonitriles by DMSO: A Rapid, Convenient Synthesis of Isocyanates

A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, −60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 10; pp. 2584 - 2585
Main Authors Le, Hoang V, Ganem, Bruce
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.05.2011
Subjects
Acetic Anhydrides
Catalysis
Dimethyl Sulfoxide - chemistry
Fluoroacetates
Isocyanates - chemical synthesis
Isocyanates - chemistry
Molecular Structure
Nitriles - chemistry
Oxidation-Reduction
Trifluoroacetic Acid - chemistry
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Summary:A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, −60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200695y