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

doi:10.1021/ja308613b

Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent

J Am Chem Soc. 2012 Oct 24;134(42):17470-3. doi: 10.1021/ja308613b. Epub 2012 Oct 15.

Authors

Jennifer L Farmer¹, Howard N Hunter, Michael G Organ

Affiliation

¹ Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, Canada M3J 1P3.

PMID: 23046477
DOI: 10.1021/ja308613b

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Boronic Acids / chemical synthesis
Boronic Acids / chemistry*
Catalysis
Coordination Complexes / chemistry*
Esters / chemical synthesis
Esters / chemistry*
Hydrocarbons, Halogenated / chemistry*
Molecular Structure
Phenols / chemistry*
Stereoisomerism

Substances

Alkenes
Boronic Acids
Coordination Complexes
Esters
Hydrocarbons, Halogenated
Phenols