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An Osmium(III)/Osmium(V) Redox Couple Generating OsV(O)(OH) Center for cis-1,2-Dihydroxylation of Alkenes with H2O2: Os Complex with a Nitrogen-Based Tetradentate Ligand

Hideki Sugimoto*, Kazuhiro Kitayama, Seiji Mori and Shinobu Itoh*

*Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email:,

H. Sugimoto, K. Kitayama, S. Mori, S. Itho, J. Am. Chem. Soc., 2012, 134, 19270-19280.

DOI: 10.1021/ja309566c


As the highly volatile OsO4 is quite toxic, the development of alternative catalysts for cis-1,2-dihydroxylation of alkenes is needed. A complex of a nitrogen-based tetradentate ligand, tris(2-pyridylmethyl)amine (tpa), and osmium acts as a very efficient turnover catalyst for syn-selective dihydroxylation of various alkenes in aqueous media using hydrogen peroxide as oxidant.

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Key Words

Upjohn Dihydroxylation, Hydrogen Peroxide

ID: J48-Y2012-3640