Modular click chemistry libraries for functional screens using a diazotizing reagent

Genyi Meng, Taijie Guo, Tiancheng Ma, Jiong Zhang, Yucheng Shen, Karl Barry Sharpless () and Jiajia Dong ()
Additional contact information
Genyi Meng: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Taijie Guo: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Tiancheng Ma: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Jiong Zhang: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Yucheng Shen: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Karl Barry Sharpless: University of the Chinese Academy of Sciences, Chinese Academy of Sciences
Jiajia Dong: University of the Chinese Academy of Sciences, Chinese Academy of Sciences

Nature, 2019, vol. 574, issue 7776, 86-89

Abstract: Abstract Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.

Date: 2019
References: Add references at CitEc
Citations: View citations in EconPapers (7)

Downloads: (external link)
https://www.nature.com/articles/s41586-019-1589-1 Abstract (text/html)
Access to the full text of the articles in this series is restricted.

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:nature:v:574:y:2019:i:7776:d:10.1038_s41586-019-1589-1

Ordering information: This journal article can be ordered from
https://www.nature.com/

DOI: 10.1038/s41586-019-1589-1

Access Statistics for this article

Nature is currently edited by Magdalena Skipper

More articles in Nature from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().