Abstract
AbstractDirect deoxyazidation of alcohols with NaN3 is a straightforward method for the synthesis of widely used alkyl azides in organic chemistry. However, known methods have some limitations such as high reaction temperatures and narrow substrate scope. Herein, a general and practical method for the preparation of alkyl azides from alcohols using NaN3 has been developed. N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) plays an important role in this deoxyazidation process, which converts a broad range of alcohols into alkyl azides at room temperature. The power of this deoxyazidation protocol has been demonstrated by successful late-stage deoxyazidation of natural products and pharmaceutically relevant molecules.
Funder
National Natural Science Foundation of China
Publisher
Springer Science and Business Media LLC
Subject
General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary
Reference61 articles.
1. Bräse, S. & Banert, K. Organic Azides: Syntheses and Applications (Wiley, 2010).
2. Patai, S. The Chemistry of the Azide Group (Interscience, 1971).
3. Bayley, H. & Knowles, J. R. Photoaffinity labeling. Methods Enzymol. 46, 69–114 (1977).
4. Bayley, H. Photogenerated Reagents in Biochemistry and Molecular Biology (Elsevier, 1983).
5. Fedan, J. S., Hogaboom, G. K. & O’Donnell, J. P. Photoafflnity labeling as pharmacological tools. Biochem. Pharmacol. 33, 1167–1180 (1984).
Cited by
9 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献