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 |
|---|---|
| Pages (from-to) | 5909-5915 |
| Number of pages | 7 |
| Journal | Organometallics |
| Volume | 24 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2005 Nov 21 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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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 journal › Article
}
TY - JOUR
T1 - Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes
AU - Yeh, Ming Chang P.
AU - Tsao, Wen Cheng
AU - Tu, Ling Hsien
PY - 2005/11/21
Y1 - 2005/11/21
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 (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.
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 (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.
UR - http://www.scopus.com/inward/record.url?scp=28944432879&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=28944432879&partnerID=8YFLogxK
U2 - 10.1021/om058043h
DO - 10.1021/om058043h
M3 - Article
AN - SCOPUS:28944432879
VL - 24
SP - 5909
EP - 5915
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 24
ER -