Aerobic Palladium-Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite

Zachary K. Wickens, Pablo E. Guzman, Robert H. Grubbs

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Catalytic 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.
Original languageEnglish (US)
Pages (from-to)236-240
Number of pages5
JournalANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume54
Issue number1
DOIs
StatePublished - 2015
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2021-10-08
Acknowledgements: We 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis

Fingerprint

Dive into the research topics of 'Aerobic Palladium-Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite'. Together they form a unique fingerprint.

Cite this