Aerobic Palladium-Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite
Permanent link to this recordhttp://hdl.handle.net/10754/672264
MetadataShow full item record
AbstractCatalytic nitrite was found to enable carbon-oxygen bond-forming reductive elimination from unstable alkyl palladium intermediates, providing dioxygenated products from alkenes. Avariety of functional groups were tolerated, and high yields (up to 94%) were observed with many substrates, also for a multigram-scale reaction. Nitrogen dioxide, which could form from nitrite under the reaction conditions, was demonstrated to be a potential intermediate in the catalytic cycle. Furthermore, the reductive elimination event was probed with 18O-labeling experiments, which demonstrated that both oxygen atoms in the difunctionalized products were derived from one molecule of acetic acid.
CitationWickens, Z. K., Guzmán, P. E., & Grubbs, R. H. (2014). Aerobic Palladium-Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite. Angewandte Chemie International Edition, 54(1), 236–240. doi:10.1002/anie.201408650
SponsorsWe gratefully acknowledge financial support from the King Abdullah University of Science and Technology Centre in Development, King Fahd University of Petroleum and Minerals, the NSF (CHE 1212767), NIH (R01GM031332), and the Gordon and Betty Moore Foundation. P.E.G. is grateful to the NIH for a postdoctoral fellowship.