Work

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

Year: 2016

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6b02132

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

Institution: University of California, Merced

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

OpenAlex ID: W2346412082

FWCI: 8.803

Cites: 32

Cited by: 228

Related to: 10