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Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

ABSTRACT: Pd(II)-catalyzed ?-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing ?-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.

SUBMITTER: Yoo EJ

PROVIDER: S-EPMC3135760 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Yoo Eun Jeong EJ Wasa Masayuki M Yu Jin-Quan JQ

Journal of the American Chemical Society 20101117 49

Pd(II)-catalyzed β-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclo ...[more]

PMID: 21082838

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