An efficient continuous flow approach to furnish furan-based biaryls

Trieu N. Trinh, Lacey Hizartzidis, Andrew J. S. Lin, David G. Harman, Adam McCluskey, Christopher P. Gordon

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

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 CatCartâ„¢ FC1032â„¢. 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 CatCartâ„¢ 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.
Original languageEnglish
Pages (from-to)9562-9571
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number47
DOIs
Publication statusPublished - 2014

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