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; Gang Dong

doi:10.1021/jo0492618

Pd-catalyzed cross-coupling of Baylis-Hillman acetate adducts with bis(pinacolato)diboron: an efficient route to functionalized allyl borates

J Org Chem. 2004 Aug 20;69(17):5807-9. doi: 10.1021/jo0492618.

Authors

George W Kabalka¹, Bollu Venkataiah, Gang Dong

Affiliation

¹ The University of Tennessee, Departments of Chemistry and Radiology, Knoxville, Tennessee 37996-1600, USA. kabalka@utk.edu

PMID: 15307766
DOI: 10.1021/jo0492618

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.