N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes
2015 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 3, 636-639 p.Article in journal (Refereed) Published
Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.
Place, publisher, year, edition, pages
2015. Vol. 17, no 3, 636-639 p.
IdentifiersURN: urn:nbn:se:kth:diva-161608DOI: 10.1021/ol503655aISI: 000349274200062PubMedID: 25616121ScopusID: 2-s2.0-84922590611OAI: oai:DiVA.org:kth-161608DiVA: diva2:797946
QC 201503252015-03-252015-03-132015-09-03Bibliographically approved