Authors
Eun Jeong Yoo, Mårten Ahlquist, Imhyuck Bae, K Barry Sharpless, Valery V Fokin, Sukbok Chang
Publication date
2008/7/18
Journal
The Journal of Organic Chemistry
Volume
73
Issue
14
Pages
5520-5528
Publisher
American Chemical Society
Description
Combined analyses of experimental and computational studies on the Cu-catalyzed three-component reactions of sulfonyl azides, terminal alkynes and amines, alcohols, or water are described. A range of experimental data including product distribution ratio and trapping of key intermediates support the validity of a common pathway in the reaction of 1-alkynes and two distinct types of azides substituted with sulfonyl and aryl(alkyl) groups. The proposal that bimolecular cycloaddition reactions take place initially between triple bonds and sulfonyl azides to give N-sulfonyl triazolyl copper intermediates was verified by a trapping experiment. The main reason for the different outcome from reactions between sulfonyl and aryl(alkyl) azides is attributed to the lability of the N-sulfonyl triazolyl copper intermediates. These species are readily rearranged to another key intermediate, ketenimine, into which various …
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EJ Yoo, M Ahlquist, I Bae, KB Sharpless, VV Fokin… - The Journal of Organic Chemistry, 2008