4.8 Article

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

Journal

ORGANIC LETTERS
Volume 13, Issue 10, Pages 2584-2585

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol200695y

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Funding

  1. NIH [GM 008500, RR02002]
  2. NSF [CHE 7904825, PGM 8018643]

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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 degrees 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.

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