Skip to main content
Open Access Publications from the University of California

Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor.

  • Author(s): Cummings, Steven P
  • Le, Thanh-Ngoc
  • Fernandez, Gilberto E
  • Quiambao, Lorenzo G
  • Stokes, Benjamin J
  • et al.

There are few examples of catalytic transfer hydrogenations of simple alkenes and alkynes that use water as a stoichiometric H or D atom donor. We have found that diboron reagents efficiently mediate the transfer of H or D atoms from water directly onto unsaturated C-C bonds using a palladium catalyst. This reaction is conducted on a broad variety of alkenes and alkynes at ambient temperature, and boric acid is the sole byproduct. Mechanistic experiments suggest that this reaction is made possible by a hydrogen atom transfer from water that generates a Pd-hydride intermediate. Importantly, complete deuterium incorporation from stoichiometric D2O has also been achieved.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.

Main Content
Current View