Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes

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Abstract

Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes proceeded in different reaction paths depending on the structure of the starting substrates. With cyclic 7-hydroxy-1,3-dienes, the reaction proceeded via insertion of the olefin into the Pd-O bond of a postulated Pd(Ar)(OR)-olefin complex to give a (η1-allyl)palladium intermediate, which underwent η131 allylic rearrangement followed by C - C bond-forming reductive elimination to afford overall 1,4-alkoxyarylation products, while with acyclic 7-hydroxy-1,3-dienes, the reaction produced 1,2-alkoxyarylation products under the same reaction conditions. The 1,2-alkoxyarylation products resulted from insertion of the olefin into either the Pd-C or the Pd-O bond of the postulated Pd(Ar)(OR)-olefm complex followed by reductive elimination.

Original languageEnglish
Pages (from-to)5909-5915
Number of pages7
JournalOrganometallics
Volume24
Issue number24
DOIs
Publication statusPublished - 2005 Nov 21

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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