TBAI Mediated Oxidative Azidation

Tetra-n-butylammonium Iodide Catalyzed C–H Azidation of Aldehydes with Thermally Stable Azidobenziodoxolone

Yukino Shinomoto^†, Akira Yoshimura^‡, Hisato Shimizu^†, Mutsumi Yamazaki^†, Viktor V. Zhdankin^‡, and Akio Saito^*†

^† Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

^‡ Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States

Org. Lett., 2015, 17 (21), pp 5212–5215

DOI: 10.1021/acs.orglett.5b02543

Publication Date (Web): October 22, 2015

Copyright © 2015 American Chemical Society

*E-mail: akio-sai@cc.tuat.ac.jp.

Abstract

 

 

 

 

 

 

 

 

 

Tetra-n-butylammonium iodide can efficiently catalyze direct azidation of aldehyde C–H bonds with thermally stable azidobenziodoxolone at room temperature. Compared to conventional methods, which require excessive amounts of highly explosive azide sources, this is a safe and convenient procedure.

Supporting Information

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.5b02543.

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• ChemInform Abstract: Tetra-n-butylammonium Iodide Catalyzed C-H Azidation of Aldehydes with Thermally Stable Azidobenziodoxolone.

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Article Views: 2,694 Times

Received 3 September 2015

Published online 22 October 2015

Published in print 6 November 2015

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