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Issue 47, 2014
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An efficient continuous flow approach to furnish furan-based biaryls

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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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Supplementary files

Article information


Submitted
01 Aug 2014
Accepted
10 Oct 2014
First published
13 Oct 2014

Org. Biomol. Chem., 2014,12, 9562-9571
Article type
Paper
Author version available

An efficient continuous flow approach to furnish furan-based biaryls

T. N. Trinh, L. Hizartzidis, A. J. S. Lin, D. G. Harman, A. McCluskey and C. P. Gordon, Org. Biomol. Chem., 2014, 12, 9562
DOI: 10.1039/C4OB01641F

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