Convenient and Efficient Pd-Catalyzed Regioselective Oxyfunctionalization of Terminal Olefins by Using Molecular Oxygen as Sole Reoxidant
Takato Mitsudome, Takuya Umetani, Naoya Nosaka, Kohsuke Mori, Tomoo Mizugaki, Kohki Ebitani, Kiyotomi Kaneda*
*Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan, Email: kanedacheng.es.osaka-u.ac.jp
T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Angew. Chem. Int. Ed., 2006, 45, 481-485.
DOI: 10.1002/anie.200502886
Abstract
The combination of PdCl2 and DMA allows highly effective oxygenation of terminal olefins under cocatalyst-free conditions. The use of a different nucleophile (H2O, AcOH) can lead to a complete switch in regioselectivity between C1 and C2 positions.
see article for more examples
see article for more reactions
Key Words
acetoxylation, alkenes, oxygen, palladium, Wacker oxidation
ID: J06-Y2006-040