An efficient continuous flow approach to furnish furan-based biaryls - PubMed (original) (raw)

. 2014 Dec 21;12(47):9562-71.

doi: 10.1039/c4ob01641f. Epub 2014 Oct 21.

Affiliations

• PMID: 25333944
• DOI: 10.1039/c4ob01641f

An efficient continuous flow approach to furnish furan-based biaryls

Trieu N Trinh et al. Org Biomol Chem. 2014.

Abstract

Suzuki cross-couplings of 5-formyl-2-furanylboronic acid with activated or neutral aryl bromides were performed under continuous flow conditions in the presence of (Bu)4N(+)F(-) and the immobilised t-butyl based palladium catalyst CatCart™ FC1032™. Deactivated aryl bromides and activated aryl chlorides were cross-coupled with 5-formyl-2-furanylboronic in the presence of (Bu)4N(+)OAc(-) using the bis-triphenylphosphine CatCart™ PdCl2(PPh3)2-DVB. Initial evidence indicates the latter method may serve as a universal approach to conduct Suzuki cross-couplings with the protocol successfully employed in the synthesis of the current gold standard Hedgehog pathway inhibitor LDE225.

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