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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.
Abstract

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.

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