Catalytic Dihydroxylation of Olefins with Hydrogen Peroxide: An Organic-Solvent- and Metal-Free System
Yoko Usui, Kazuhiko Sato*, Masato Tanaka
*Research Institute for Green Technology, National Institute of Advanced
Industrial Science and Technology (AIST), Tsukuba Central, Email:
k.satoaist.go.jp
Y. Usui, K. Sato, M. Tanaka, Angew. Chem. Int. Ed., 2003, 42, 5623-5625.
DOI: 10.1002/anie.200352568
Abstract
A clean and safe method for the dihydroxylation of alkenes under organic-solvent- and metal-free conditions was developed. The resin-supported sulfonic acid catalyst is easily recycled.
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Details
The document discusses a green chemistry method for the catalytic dihydroxylation of olefins using hydrogen peroxide (H2O2) without organic solvents or metals. This method, developed by Yoko Usui, Kazuhiko Sato, and Masato Tanaka, focuses on producing 1,2-diols, which are valuable intermediates in various industries. Traditional methods using metal oxides and organic solvents have low atom efficiency and generate significant waste. In contrast, H2O2 is an ideal oxidant due to its high atom efficiency and water as the sole by-product. The researchers used resin-supported sulfonic acid (nafion NR50) as a catalyst, achieving high yields and selectivity for 1,2-diols. The catalyst is easily recyclable, maintaining over 94% yield across ten cycles. The method is effective for both internal and terminal olefins, with higher reactivity observed for internal olefins. The process involves two steps: epoxidation of the olefin followed by hydration of the epoxide. This approach offers a clean, safe, and efficient alternative for dihydroxylation, aligning with green chemistry principles. The study highlights the potential of resin-supported sulfonic acids as superior catalysts compared to homogeneous acid catalysts.
Key Words
alkenes, dihydroxylation, green chemistry, hydrogen peroxide, oxidation
ID: J06-Y2003-820