Literature DB >> 21491899

Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.

Hoang V Le1, Bruce Ganem.   

Abstract

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.

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Year:  2011        PMID: 21491899      PMCID: PMC3102642          DOI: 10.1021/ol200695y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Stereospecific synthesis of the alpha- and beta-D-glucopyranosyl ureas.

Authors:  Y Ichikawa; T Nishiyama; M Isobe
Journal:  J Org Chem       Date:  2001-06-15       Impact factor: 4.354

2.  A new approach to the neoglycopeptides: synthesis of urea- and carbamate-tethered N-acetyl-D-glucosamine amino acid conjugates.

Authors:  Yoshiyasu Ichikawa; Fumiyo Ohara; Hiyoshizo Kotsuki; Keiji Nakano
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

  2 in total
  3 in total

1.  Mild oxidation of tosylmethylisocyanide to tosylmethylisocyanate: utility in synthetic and medicinal chemistry.

Authors:  Hoang V Le; Bruce Ganem
Journal:  Tetrahedron Lett       Date:  2014-03-19       Impact factor: 2.415

2.  A Practical Synthesis of Isocyanates from Isonitriles: Ethyl 2-Isocyanatoacetate.

Authors:  Hoang V Le; Bruce Ganem
Journal:  Organic Synth       Date:  2012-04-05

3.  Urea Derivatives in Modern Drug Discovery and Medicinal Chemistry.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  J Med Chem       Date:  2019-12-02       Impact factor: 7.446

  3 in total

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