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Nickel-catalyzed synthesis of acrylamides from alpha-olefins and isocyanates.

ABSTRACT: [reaction: see text] The nickel(0)-catalyzed coupling of alpha-olefins and isocyanates proceeds in the presence of the N-heterocyclic carbene ligand IPr to provide alpha,beta-unsaturated amides. Carbon-carbon bond formation occurs preferentially at the 2-position of the olefin. The N-tert-butyl amide products can be converted to the corresponding primary amides under acidic conditions.

SUBMITTER: Schleicher KD

PROVIDER: S-EPMC3148187 | biostudies-literature | 2007 Mar

REPOSITORIES: biostudies-literature

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Nickel-catalyzed synthesis of acrylamides from alpha-olefins and isocyanates.

Schleicher Kristin D KD Jamison Timothy F TF

Organic letters 20070202 5

[reaction: see text] The nickel(0)-catalyzed coupling of alpha-olefins and isocyanates proceeds in the presence of the N-heterocyclic carbene ligand IPr to provide alpha,beta-unsaturated amides. Carbon-carbon bond formation occurs preferentially at the 2-position of the olefin. The N-tert-butyl amide products can be converted to the corresponding primary amides under acidic conditions. ...[more]

PMID: 17269783

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