- Title
- An efficient continuous flow approach to furnish furan-based biaryls
- Creator
- Trinh, Trieu N.; Hizartzidis, Lacey; Lin, Andrew J. S.; Harman, David G.; McCluskey, Adam; Gordon, Christopher P.
- Relation
- NHMRC|1021156 http://purl.org/au-research/grants/nhmrc/1021156
- Relation
- Organic & Biomolecular Chemistry Vol. 12, p. 9562-9571
- Publisher Link
- http://dx.doi.org/10.1039/c4ob01641f
- Publisher
- Royal Society Chemistry
- Resource Type
- journal article
- Date
- 2014
- Description
- 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.
- Subject
- furan-based biaryls; kinase inhibitors; Suzuki cross-couplings; Hedgehog pathway inhibitor LDE225
- Identifier
- http://hdl.handle.net/1959.13/1299368
- Identifier
- uon:19862
- Identifier
- ISSN:1477-0520
- Language
- eng
- Full Text
- Reviewed
- Hits: 1722
- Visitors: 2469
- Downloads: 474
| Thumbnail | File | Description | Size | Format | |||
|---|---|---|---|---|---|---|---|
| View Details Download | ATTACHMENT02 | Author final version | 483 KB | Adobe Acrobat PDF | View Details Download |