Pd-Catalyzed Cross-Coupling of Baylis-Hillman Acetate Adducts with Bis(pinacolato)diboron: An Efficient Route to Functionalized Allyl Borates
George W. Kabalka*, Bollu Venkataiah and Gang Dong
*The University of Tennessee, Departments of Chemistry and Radiology,
Knoxville, Tennessee 37996-1600, Email: kabalka
utk.edu
G. W. Kabalka B. Venkataiah, G. Dong, J. Org. Chem., 2004, 69, 5807-5809.
DOI: 10.1021/jo0492618 (free Supporting Information)
see article for more examples
Abstract
3-Substituted-2-alkoxycarbonyl allylboronates are readily produced by the cross-coupling of Baylis-Hillman acetate adducts and bis(pinacolato)diboron in the presence of a palladium catalyst. Subsequent addition of excess aqueous KHF2 gives stable allyl trifluoroborate salts. Allylboronate and allyltrifluoroborate derivatives react stereoselectively with aldehydes to afford functionalized homoallylic alcohols.
see article for more reactions
Key Words
Potassium Allyltrifluoroborates, Palladium Catalysis, Homoallylic Alcohols
ID: J42-Y2004-660
