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: kabalkautk.edu

G. W. Kabalka B. Venkataiah, G. Dong, J. Org. Chem., 2004, 69, 5807-5809.

DOI: 10.1021/jo0492618

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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.

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Key Words

Potassium Allyltrifluoroborates, Palladium Catalysis, Homoallylic Alcohols

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ID: J42-Y2004-660