Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

Pratik P. Goswami, Victoria P. Suding, Angela S. Carlson, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.

Original languageEnglish (US)
Pages (from-to)4805-4809
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number28
DOIs
StatePublished - Oct 2016

Bibliographical note

Funding Information:
We thank Amy Ott for acquiring mass spectra. The American Chemical Society ? Petroleum Research Fund (ACS-PRF) (PRF#56505-DNI1) and the University of Minnesota are thanked for financial support. V. P. S. acknowledges the University of Minnesota ? Undergraduate Research Opportunity (UMN-UROP) for support.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Keywords

  • Amines
  • Azides
  • Click chemistry
  • Green chemistry

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