Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 48, Pages 17407-17415Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603626
Keywords
anilines; diazotization; cross-coupling; flow conditions; sustainable chemistry
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Funding
- NSERC Canada
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The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki-Miyaura and Sonogashira cross-coupled products.
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