Palladium-Catalyzed Olefin Dioxygenation

A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and PhI(OAc)2 as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-03, Vol.130 (10), p.2962-2964
Main Authors: Li, Yang, Song, Datong, Dong, Vy M
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Alkenes - chemistry
Catalysis
Esters - chemical synthesis
Esters - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Osmium - chemistry
Oxidation-Reduction
Oxygen - chemistry
Palladium - chemistry
Stereoisomerism
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Summary:A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and PhI(OAc)2 as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An 18O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja711029u