Use of tricyclohexylphosphine to control regiochemistry in palladium-catalyzed allylic alkylation

Authors
Blacker, AJ Clarke, ML Loft, MS Williams, JMJ
Citation
Aj. Blacker et al., Use of tricyclohexylphosphine to control regiochemistry in palladium-catalyzed allylic alkylation, ORG LETT, 1(12), 1999, pp. 1969-1971
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
12
Year of publication
1999
Pages
1969 - 1971
Database
ISI
SICI code
1523-7060(199912)1:12<1969:UOTTCR>2.0.ZU;2-V
Abstract
[GRAPHICS] Tricyclohexylphosphine, Cy3P, in conjuction with [(C3H5)PdCl](2) catalyzes allylic alkylation of terminal allylic acetates with high regioselectivity toward branched products, which is in contrast to most other palladium cata lysts. Other ligands, even those of similar basicity or bulkiness, did not show the same regioselectivity. Alkylation of 1,4-diacetoxy-2-butene gave p redominantly branched products which had not been observed previously.