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Regioselective Cross-Coupling of Allylboronic Acid Pinacol Ester Derivatives with Aryl Halides via Pd-PEPPSI-IPent

Jennifer L. Farmer, Howard N. Hunter and Michael G. Organ*

*Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, Canada M3J 1P3, Email: organyorku.ca

J. L. Farmer, H. N. Hunter, M. G. Organ, J. Am. Chem. Soc., 2012, 134, 17470-17473.

DOI: 10.1021/ja308613b (free Supporting Information)



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Abstract

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and aqueous KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed.

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Key Words

allylation, Suzuki coupling


ID: J48-Y2012-3370