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N,N-diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes.

ABSTRACT: 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.

SUBMITTER: Xie S

PROVIDER: S-EPMC4334907 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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N,N-diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes.

Xie Sheng S Ramström Olof O Yan Mingdi M

Organic letters 20150123 3

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 de ...[more]

PMID: 25616121

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