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A Tin–Tungsten Mixed Oxide as an Efficient Heterogeneous Catalyst for CC Bond-Forming Reactions

✍ Scribed by Yoshiyuki Ogasawara; Sayaka Uchida; Kazuya Yamaguchi; Noritaka Mizuno


Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
301 KB
Volume
15
Category
Article
ISSN
0947-6539

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✦ Synopsis


Abstract

Mix and calcinate: The tin–tungsten mixed oxide (Sn–W oxide) prepared by calcination of the Sn–W hydroxide at 800 °C acts as an effective and reusable solid catalyst for CC bond‐forming reactions, such as the cyclization of citronellal, the Diels–Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (see scheme). The observed catalysis was truly heterogeneous, and the recovered catalyst could be reused without loss of its high catalytic performance.magnified image

The tin–tungsten mixed oxide prepared by the calcination of the tin–tungsten hydroxide precursor with a Sn/W molar ratio of 2 at 800 °C (SnW2–800) acts as an effective and reusable solid catalyst for CC bond‐forming reactions, such as the cyclization of citronellal, the Diels–Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (TMSCN). Various kinds of structurally diverse aliphatic, aromatic, and unsaturated, heteroatom‐containing substrates could be converted into the desired products in high to excellent yields. The observed catalyses for these reactions were truly heterogeneous and the recovered catalyst could be reused several times without an appreciable loss of its high catalytic performance. The Brønsted acid sites generated on the aggregated polytungstate species on SnW2–800 likely play an important role in the CC bond‐forming reactions.


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