Copper(II)-catalyzed allylation of propargylic and allylic alcohols by allylsilanes: a facile synthesis of 1,5-enynes

Propargylic alcohols undergo smooth deoxygenative allylation with allylsilanes in the presence of a solution of 10 mol % of copper(II) tetrafluoroborate in acetonitrile to afford the corresponding 1,5-enynes in good to high yields under mild and neutral conditions. Scandium triflate is also found to...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2008-01, Vol.49 (4), p.614-618
Main Authors: Yadav, J.S., Subba Reddy, B.V., Srinivasa Rao, T., Raghavendra Rao, K.V.
Format: Article
Language:English
Subjects:
1,5-Enynes
Allylation
Allylic alcohols
Cu(II) reagents
Propargylic alcohols
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Propargylic alcohols undergo smooth deoxygenative allylation with allylsilanes in the presence of a solution of 10 mol % of copper(II) tetrafluoroborate in acetonitrile to afford the corresponding 1,5-enynes in good to high yields under mild and neutral conditions. Scandium triflate is also found to catalyze efficiently the nucleophilic substitution of propargylic alcohols with allylsilanes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.11.143