Journal
ORGANIC LETTERS
Volume 17, Issue 3, Pages 636-639Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503655a
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Funding
- Royal Institute of Technology
- National Institutes of Health [R01GM080295]
- National Science Foundation [CHE-1112436]
- China Scholarship Council
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1112436] Funding Source: National Science Foundation
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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.
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