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Pd-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Bis(pinacolato)diboron: An Efficient Route to Functionalized Allyl Borates

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George W. Kabalka,* Bollu Venkataiah, and Gang Dong

The University of Tennessee, Departments of Chemistry and Radiology, Knoxville, Tennessee 37996-1600 kabalka@utk.edu

J. Org. Chem., 2004, 69 (17), pp 5807–5809

DOI: 10.1021/jo0492618

Publication Date (Web): July 29, 2004

Section:

Organometallic and Organometalloidal Compounds

Abstract

The cross-coupling of Baylis−Hillman acetate adducts and bis(pinacolato)diboron proceeds readily in high yields in the presence of palladium catalyst to produce 3-substituted-2-alkoxycarbonyl allylboronates. These allylboronates can be transformed to stable allyl trifluoroborate salts by addition of excess aqueous KHF₂. Both the allylboronate and allyltrifluoroborate derivatives react with aldehydes to afford functionalized homoallylic alcohols stereoselectively.

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Citing Articles

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This article has been cited by 14 ACS Journal articles (5 most recent appear below).

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