Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 29, Pages 6418-6430Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402804
Keywords
Flow chemistry; Gas-liquid microreactor; Palladium catalysis; Carbonylation; C C bond formation
Categories
Funding
- Georganics Ltd.
- German Academic Exchange Service (DAAD)
- Sanofi-Aventis
- CSIRO Material Science and Engineering
- Clayton, Australia
- Engineering and Physical Sciences Research Council (EPSRC)
- [BP 1702]
- EPSRC [EP/F069685/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/F069685/1] Funding Source: researchfish
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A series of continuous flow chemistry processes that facilitate the palladium-catalysed carbonylation of aryl and vinyl iodides and aryl bromides with a range of alkoxy, hydroxy and amino nucleophiles is reported. Harnessing a semipermeable Teflon (R) AF-2400 Tube-in-Tube assembly, these reactors permit the controlled transport of carbon monoxide into solution at elevated pressure to generate homogeneous flow streams, avoiding some potential issues associated with segmented flow gas-liquid reactors. As the volume of pressurised gas contained within the device is low, the hazards associated with this are potentially mitigated relative to comparable batch processes. We also show how the incorporation of a second in-line gas-flow reactor allows for the sequential introduction of two gases (carbon monoxide and a gaseous nucleophile) into the reaction stream.
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