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Sustainable HandaPhos-ppm Palladium Technology for Copper-Free Sonogashira Couplings in Water under Mild Conditions

Sachin Handa*, Justin D. Smith, Yitao Zhang, Balaram S. Takale, Fabrice Gallou and Bruce H. Lipshutz*

*University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292; University of California, Santa Barbara, California 93106, Email:,

S. Handa, J. D. Smith, Y. Zhang, B. S. Takale, F. Gallou, B. H. Lipshutz, Org. Lett., 2018, 20, 542-545.

DOI: 10.1021/acs.orglett.7b03621 (free Supporting Information)

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Complexation of Pd(OAc)2 with HandaPhos as ligand leads to a precatalyst that efficiently mediates Sonogashira couplings in aqueous nanomicelles under very mild conditions. Neither organic solvent nor copper is required. After isolution of the product, the reaction mixture that can be recycled without additional additives.

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Key Words

Sonogashira coupling, alkynylation, green chemistry

ID: J54-Y2018