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Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: Dichotomy via a common pathway
Department of Chemistry, Skaggs Institute of Chemical Biology, Scripps Research Institute.ORCID iD: 0000-0002-1553-4027
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2008 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 14, 5520-5528 p.Article in journal (Refereed) Published
Abstract [en]

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 nucleophiles such as amines, alcohols, or water add to afford the three-component coupled products: amidines, imidates, or amides, respectively. In addition, the proposed mechanistic framework is in good agreement with the obtained kinetics and competition studies. A computational study (B3LYP/LACV3P*+) was also performed confirming the proposed mechanistic pathway that the triazolyl copper intermediate plays as a branching point to dictate the product distribution.

Place, publisher, year, edition, pages
2008. Vol. 73, no 14, 5520-5528 p.
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Organic Chemistry
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URN: urn:nbn:se:kth:diva-48876DOI: 10.1021/jo800733pISI: 000257543100039OAI: oai:DiVA.org:kth-48876DiVA: diva2:488421
Note
QC 20120202Available from: 2012-02-01 Created: 2011-11-23 Last updated: 2017-12-08Bibliographically approved

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Ahlquist, Mårten

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