4.6 Article

An efficient continuous flow approach to furnish furan-based biaryls

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 12, 期 47, 页码 9562-9571

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01641f

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资金

  1. Australian Cancer Research Foundation
  2. Australian Research Council
  3. ARC DECRA fellowship
  4. University of Newcastle
  5. Prime Minister's Australia Asia Postgraduate Award

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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)(4)N+F- and the immobilised t-butyl based palladium catalyst CatCart (TM) FC1032 (TM). Deactivated aryl bromides and activated aryl chlorides were cross-coupled with 5-formyl-2-furanylboronic in the presence of (Bu)(4)N+OAc- using the bis-triphenylphosphine CatCart (TM) 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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