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An efficient continuous flow approach to furnish furan-based biaryls†
Trieu N. Trinh,Lacey Hizartzidis,Andrew J. S. Lin,Adam McCluskey,Christopher P. Gordon
Organic & Biomolecular Chemistry Pub Date : 10/13/2014 00:00:00 , 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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