Organic Chemistry Portal



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

Steven P. Cummings, Thanh-Ngoc Le, Gilberto E. Fernandez, Lorenzo G. Quiambao and Benjamin J. Stokes*

*School of Natural Sciences, University of California, Merced, 5200 North Lake Road, Merced, California 95343, United States, Email:

S. P. Cummings, T.-N. Le, G. E. Fernandez, L. G. Quiambao, B. J. Stokes, J. Am. Chem. Soc., 2016, 138, 6107-6110.

DOI: 10.1021/jacs.6b02132 (free Supporting Information)

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words


ID: J48-Y2016