An efficient continuous flow approach to furnish furan-based biaryls?

Organic & Biomolecular Chemistry Pub Date: 2014-10-13 DOI: 10.1039/C4OB01641F

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.

Graphical abstract: An efficient continuous flow approach to furnish furan-based biaryls
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