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

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 (η 1 -allyl)palladium intermediate, which underwent η 131 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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Palladium
Alkenes
dienes
Bromides
palladium
bromides
alkenes
insertion
elimination
products
Substrates

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes. / Yeh, Ming-Chang P.; Tsao, Wen Cheng; Tu, Ling-Hsien.

In: Organometallics, Vol. 24, No. 24, 21.11.2005, p. 5909-5915.

Research output: Contribution to journalArticle

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N2 - 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 (η 1 -allyl)palladium intermediate, which underwent η 1 -η 3 -η 1 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.

AB - 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 (η 1 -allyl)palladium intermediate, which underwent η 1 -η 3 -η 1 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.

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