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

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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.

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Key Words

acetoxylation, alkenes, oxygen, palladium, Wacker oxidation

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ID: J06-Y2006-040