Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes

Dan Yang* and Chi Zhang

*Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, Email: yangdanhku.hk

D. Yang, C. Zhang, J. Org. Chem., 2001, 66, 4814-4818.

DOI: 10.1021/jo010122p

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Abstract

Specific oxidation protocols have been developed for the cleavage of styrenes, aliphatic olefins, and terminal aliphatic olefins to carbonyl compounds with ruthenium trichloride as catalyst. Olefins that are not fully substituted are converted to aldehydes rather than carboxylic acids.

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Details

The document details the development of three ruthenium-catalyzed oxidative cleavage protocols for converting olefins to aldehydes. The first protocol uses RuCl₃-Oxone-NaHCO₃ in a CH₃CN-H₂O solvent system, effectively cleaving aryl olefins to aromatic aldehydes and some aliphatic olefins to alkyl aldehydes. The second protocol employs RuCl₃-NaIO₄ in a 1,2-dichloroethane-H₂O system, which is particularly effective for disubstituted and trisubstituted aliphatic olefins, yielding dialdehydes and keto aldehydes. The third protocol uses RuCl₃-NaIO₄ in a CH₃CN-H₂O system, optimized for monosubstituted aliphatic olefins, providing high yields of aldehydes. These methods offer safer and more convenient alternatives to traditional oxidative cleavage methods, such as those using osmium tetraoxide, and are expected to be useful in organic synthesis due to the ease of handling and lower toxicity of ruthenium trichloride. The document also includes experimental procedures and results, demonstrating the efficiency and selectivity of these protocols across various olefin substrates.

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Ruthenium-Catalyzed Oxidative Cleavage of Alkynes to Carboxylic Acids

D. Yang, F. Chen, Z.-M. Dong, D.-W. Zhang, J. Org. Chem., 2004, 69, 209-212.

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Key Words

Oxidation, Oxidative Cleavage, Oxone, Ruthenium, Sodium Periodate, Aldehydes, Ketones, Carboxylic Acids

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ID: J42-Y2001-270