4.6 Article

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

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 17, Pages 4343-4349

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802536

Keywords

cyanosilylation; cyclization; Diels-Alder reactions; heterogenenous catalysis; tin; tungsten

Funding

  1. Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering)
  2. Japan Science and Technology Agency (JST)
  3. Ministry of Education, Culture, Sports, Science and Technology

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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 degrees 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 Bronsted 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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