Chemical libraries from a double click

Because the CuAAC reaction fulfils all of the click criteria, it has become the poster child for click chemistry. Alternatively, azides can be prepared from primary amines (compounds that contain NH2 groups) by a 'diazotransfer' reaction. [...]the state-of-the-art reagent used to carry out...

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Bibliographic Details
Published in:Nature (London) 2019-10, Vol.574 (7776), p.42-43
Main Authors: Topczewski, Joseph J, Liu, En-Chih
Format: Article
Language:English
Subjects:
Amines
Azide
Chemical bonds
Chemical synthesis
Chemistry
Organic chemistry
Reagents
Substrates
Online Access:Get full text
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Summary:Because the CuAAC reaction fulfils all of the click criteria, it has become the poster child for click chemistry. Alternatively, azides can be prepared from primary amines (compounds that contain NH2 groups) by a 'diazotransfer' reaction. [...]the state-of-the-art reagent used to carry out diazotransfer had been trifluoromethanesulfonyl azide11 (CF3SO2N3). The number of azides synthesized is impressive (see Supplementary Information Section 6 of the paper1 for a full list), but the most striking aspect of this study is the substrate scope: the reaction works for different amine subclasses, on complex molecules, and in the presence of various chemical groups. [...]Meng and colleagues' diazotransfer reaction meets the speed, breadth and efficiency criteria for click chemistry.
ISSN:0028-0836
1476-4687
DOI:10.1038/d41586-019-02905-w