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

31 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

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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