Multistep electron transfer in palladium-catalyzed aerobic oxidations via a metal macrocycle-quinone system
- Univ. of Uppsala (Sweden)
Selective palladium-catalyzed aerobic conditions of olefins and conjugated dienes with the aid of a metal macrocycle-quinone system have been developed. This involves a multistep electron transfer with three catalysts (Pd(OAc){sub 2}, hydroquinone, metal macrocycle). The triple catalytic system was applied to (i) 1,4-oxidation of conjugated dienes (1,4-diacetoxylation and 1,4-dialkoxylation), (ii) oxidation of terminal olefins to ketones, and (iii) allylic oxidation of cyclic olefins to 2-alken-1-yl acetates. The reactions occur under very mild conditions, (i) and (ii) at room temperature and (iii) at 60{degree}C, and are reminiscent of aerobic processes occurring in living organisms. Thus, there is an electron transfer from the substrate to Pd(II) giving Pd(0), followed by another electron transfer from Pd(0) to benzoquinone. The hydroquinone thus formed transfers electrons to the oxidized form of the metal macrocycle, which is reduced.
- OSTI ID:
- 6653744
- Journal Information:
- Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 112:13; ISSN 0002-7863; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
AEROBIC CONDITIONS
AROMATICS
CATALYSTS
CHEMICAL REACTIONS
DATA
DATA ANALYSIS
DIENES
ELECTRON TRANSFER
ELEMENTS
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDATION
PALLADIUM
PLATINUM METALS
POLYENES
QUINONES
TRANSITION ELEMENTS