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; Akio Saito

doi:10.1021/acs.orglett.5b02543

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

Org Lett. 2015 Nov 6;17(21):5212-5. doi: 10.1021/acs.orglett.5b02543. Epub 2015 Oct 22.

Authors

Yukino Shinomoto¹, Akira Yoshimura², Hisato Shimizu¹, Mutsumi Yamazaki¹, Viktor V Zhdankin², Akio Saito¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
² Department of Chemistry and Biochemistry, University of Minnesota Duluth , Duluth, Minnesota 55812, United States.

PMID: 26492530
DOI: 10.1021/acs.orglett.5b02543

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.