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A Phosphine-Mediated Conversion of Azides into Diazo Compounds†

Authors

  • †

    We thank Dr. Ilia A. Guzei and Amit Choudhary for X-ray crsytallographic data pertaining to triazene 8 and Dr. Annie Tam for preparing azide 2 d. We acknowledge use of the National Magnetic Resonance Facility (NMRFAM) and services of the Mass Spectrometry Facility in the Department of Chemistry. This work was supported by NIH grant GM044783; NMRFAM was supported by NIH grant P41RR02301.

Abstract

N2 the mild: Diazo compounds are extremely versatile intermediates for synthetic organic chemistry, but their synthesis can be challenging in the presence of delicate functional groups. The Staudinger ligation has inspired a mild method for the conversion of a broad range of azides into their diazo compound derivatives through an acyl triazene intermediate.

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DOI

10.1002/anie.200804689

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Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • azides;
  • heterocycles;
  • phosphines;
  • Staudinger reaction;
  • synthetic methods

Publication History

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  • Version of record online:
  • Manuscript Received:

Funded by

  • NIH. Grant Number: GM044783
  • NIH. Grant Number: P41RR02301

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