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 η1-η3-η1 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 language | English |
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Pages (from-to) | 5909-5915 |
Number of pages | 7 |
Journal | Organometallics |
Volume | 24 |
Issue number | 24 |
DOIs | |
Publication status | Published - 2005 Nov 21 |
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry