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Title: Aerobic C-H Acetoxylation of 8-Methylquinoline in PdII-Pyridinecarboxylic Acid Systems: Some Structure-Reactivity Relationships

Catalytic oxidative C–H acetoxylation of 8-methylquinoline as a model substrate with O 2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C–H activation and the O 2 activation steps shows that the C–H activation step is rate-limiting, whereas the O 2 activation occurs at a much faster rate already at 20 °C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C–H activation.
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  1. Univ. of Maryland, College Park, MD (United States)
Publication Date:
OSTI Identifier:
DOE Contract Number:
Resource Type:
Journal Article
Resource Relation:
Journal Name: Organometallics; Journal Volume: 32; Journal Issue: 17; Related Information: CCHF partners with University of Virginia (lead); Brigham Young University; California Institute of Technology; Colorado School of Mines; University of Maryland; University of North Carolina, Chapel Hill; University of North Texas; Princeton University; The Scripps Research Institute; Yale University
American Chemical Society (ACS)
Research Org:
Energy Frontier Research Centers (EFRC); Center for Catalytic Hydrocarbon Functionalization (CCHF)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous), catalysis (heterogeneous), bio-inspired, hydrogen and fuel cells, materials and chemistry by design, synthesis (novel materials)