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

Hoang V. Le and Bruce Ganem*

*Department of Chemistry & Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States, Email: bg18cornell.edu

H. V. Le, B. Ganem, Org. Lett., 2011, 13, 2584-2585.

DOI: 10.1021/ol200695y (free Supporting Information)


Abstract

A smooth and efficient oxidation of isonitriles to isocyanates by DMSO as the oxidant is catalyzed by trifluoroacetic anhydride. 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.

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Key Words

Isocyanates, Urea Derivatives, DMSO


ID: J54-Y2011-1470