Mechanistic Study of Alcohol Oxidation by the Pd(OAc)2/O2/DMSO Catalyst System and Implications for the Development of Improved Aerobic Oxidation Catalysts

The Pd(OAc)2/O2/DMSO catalyst system displays impressive versatility in the aerobic oxidation of organic substrates, ranging from alcohols to olefins. This report details mechanistic insights into these reactions. Dimethyl sulfoxide (DMSO) plays no redox role in the chemistry, and kinetic experiment...

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Veröffentlicht in:	Journal of the American Chemical Society 2002-02, Vol.124 (5), p.766-767
Hauptverfasser:	Steinhoff, Bradley A, Fix, Shannon R, Stahl, Shannon S
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Chemistry Exact sciences and technology Fundamental and applied biological sciences. Psychology Kinetics and mechanisms Mechanisms. Catalysis. Electron transfer. Models Molecular biophysics Organic chemistry Physical chemistry in biology Reactivity and mechanisms
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Zusammenfassung:	The Pd(OAc)2/O2/DMSO catalyst system displays impressive versatility in the aerobic oxidation of organic substrates, ranging from alcohols to olefins. This report details mechanistic insights into these reactions. Dimethyl sulfoxide (DMSO) plays no redox role in the chemistry, and kinetic experiments identify the turnover-limiting step as DMSO-promoted oxidation of palladium(0) by molecular oxygen. The “chemical oxidase” pathway characterized for this catalyst system holds great promise for the design of new aerobic oxidation reactions.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja016806w