Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione.

Journal Article (Journal Article)

Cyclization of (E)-7,8-dideuterio-7-octene-2,4-dione [(E)-1-7,8-d(2)] catalyzed by PdCl(2)(CH(3)CN)(2) (2) formed cis-2-acyl-3,4-dideuteriocyclohexanone (cis-3-3,4-d(2)) in 64% yield as the exclusive isotopomer. This experiment, in conjunction with additional deuterium labeling experiments, was in accord with a mechanism for the conversion of 1 to 3 catalyzed by 2 involving attack of the enol carbon atom on a palladium-complexed olefin followed by palladium migration and protonolysis from a palladium enolate complex.

Full Text

Duke Authors

Cited Authors

  • Qian, H; Widenhoefer, RA

Published Date

  • February 2003

Published In

Volume / Issue

  • 125 / 8

Start / End Page

  • 2056 - 2057

PubMed ID

  • 12590527

Pubmed Central ID

  • 12590527

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0293002

Language

  • eng