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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, Michael G Organ

J Am Chem Soc. 2012 Oct 24;134(42):17470-3.

PMID: 23046477

Abstract:

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and 5 M KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed (E/Z ≈ 80/20).

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