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Enantioselective N-heterocyclic carbene-catalyzed ?-hydroxylation of enals using nitroarenes: an atom transfer reaction that proceeds via single electron transfer.

ABSTRACT: A novel oxidative N-heterocyclic carbene-catalyzed reaction pathway has been discovered. Alkyl and aryl enals undergo ?-hydroxylation via oxygen atom transfer from electron-deficient nitrobenzenes, followed by trapping of the resultant acyl azolium by the solvent. The proposed mechanism involves a single electron transfer event to initiate the reaction followed by radical recombination. This represents a profound mechanistic departure from the established two-electron disconnects in NHC catalysis.

SUBMITTER: White NA

PROVIDER: S-EPMC4210054 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Enantioselective N-heterocyclic carbene-catalyzed β-hydroxylation of enals using nitroarenes: an atom transfer reaction that proceeds via single electron transfer.

White Nicholas A NA Rovis Tomislav T

Journal of the American Chemical Society 20141010 42

A novel oxidative N-heterocyclic carbene-catalyzed reaction pathway has been discovered. Alkyl and aryl enals undergo β-hydroxylation via oxygen atom transfer from electron-deficient nitrobenzenes, followed by trapping of the resultant acyl azolium by the solvent. The proposed mechanism involves a single electron transfer event to initiate the reaction followed by radical recombination. This represents a profound mechanistic departure from the established two-electron disconnects in NHC catalysi ...[more]

PMID: 25302860

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