UC Santa Barbara
ppm Pd-catalyzed, Cu-free Sonogashira couplings in water using commercially available catalyst precursors.
- Author(s): Jin, Bo
- Gallou, Fabrice
- Reilly, John
- Lipshutz, Bruce H
- et al.
Published Web Locationhttps://doi.org/10.1039/c8sc05618h
A new catalyst that derives from commercially available precursors for copper-free, Pd-catalyzed Sonogashira reactions at the sustainable ppm level of precious metal palladium under mild aqueous micellar conditions has been developed. Both the palladium pre-catalyst and ligand are commercially available, bench stable, and highly cost-effective. The catalyst is applicable to both aryl- and heteroaryl-bromides as educts. A wide range of functional groups are tolerated and the aqueous reaction medium can be recycled. An application to a key intermediate associated with an active pharmaceutical ingredient (ponatinib) is discussed.