Efficient conversion of aromatic amines into azides: a one-pot synthesis of triazole linkages

Barral, K., Moorhouse, A. D., Moses, J. E. (April 2007) Efficient conversion of aromatic amines into azides: a one-pot synthesis of triazole linkages. Org Lett, 9 (9). pp. 1809-11. ISSN 1523-7060 (Print)1523-7052

URL: https://pubmed.ncbi.nlm.nih.gov/17391043/
DOI: 10.1021/ol070527h

Abstract

[reaction: see text] An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described. The synthesis of aromatic azides from the corresponding amines is accomplished under mild conditions with tert-butyl nitrite and azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in excellent yields from a variety of aromatic amines without the need for isolation of the azide intermediates.

Item Type: Paper
Additional Information: Organic letters
Uncontrolled Keywords: Amines/*chemistry Azides/*chemical synthesis/chemistry Cross-Linking Reagents/*chemistry Molecular Structure Triazoles/*chemistry
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 26 April 2007
Date Deposited: 19 Apr 2021 21:33
Last Modified: 19 Apr 2021 21:33
Related URLs:
URI: https://repository.cshl.edu/id/eprint/39530

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