Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides
- 13 April 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (10) , 3950-3956
- https://doi.org/10.1021/jo050286w
Abstract
The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners.Keywords
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