title: Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor.
abstract: 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.
authors.affiliation: School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
authors.forename: Steven P
authors.initials: SP
authors.lastname: Cummings
authors.affiliation: School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
authors.forename: Thanh-Ngoc
authors.initials: TN
authors.lastname: Le
authors.affiliation: School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
authors.forename: Gilberto E
authors.initials: GE
authors.lastname: Fernandez
authors.affiliation: School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
authors.forename: Lorenzo G
authors.initials: LG
authors.lastname: Quiambao
authors.affiliation: School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Stokes