Journal
HELVETICA CHIMICA ACTA
Volume 102, Issue 3, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201900024
Keywords
micelles; ligands; copper-free Sonogashira cross coupling; sustainable chemistry; water
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Funding
- Novartis AG
- Swiss National Science Foundation [BSSGI0-155902/1, 175746]
- University of Basel
- NCCR Molecular Systems Engineering
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A robust and general protocol for a sustainable copper-free Sonogashira cross coupling under micellar aqueous reaction conditions with high turnover was developed. By using the commercially available catalyst CataCXium A Pd G3 and THF as co-solvent, various alkyne substrates were efficiently cross-coupled with a broad range of aryl halides, providing improved yields and low catalyst loadings. The reaction parameters were optimized to render the process operationally simple, robust and scalable. The method gives access to alkynylated arenes, heterocyclic compounds, and monofunctionalized products from dihalogenated substrates with an improved selectivity achieved by the micellar aqueous reaction conditions.
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