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An Immobilized Organocatalyst for Cyanosilylation and Epoxidation
Author(s) -
Yamaguchi Kazuya,
Imago Toru,
Ogasawara Yoshiyuki,
Kasai Jun,
Kotani Miyuki,
Mizuno Noritaka
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606124
Subject(s) - chemistry , trimethylsilyl cyanide , catalysis , heterogeneous catalysis , hydrogen peroxide , hydroxide , trimethylsilyl , organic chemistry , polymer chemistry , combinatorial chemistry
An immobilized organocatalyst has been synthesized by covalently anchoring an N ‐octyldihydroimidazolium hydroxide fragment onto SiO 2 (denoted as 1 ‐OH/SiO 2 ). This catalyst exhibits high catalytic performance for the cyanosilylation of various carbonyl compounds with trimethylsilyl cyanide (Me 3 SiCN). The effectiveness of the system is evidenced by the high to excellent yields of the corresponding trimethylsilyl ethers under mild reaction conditions, which are superior to those obtained with commercially available MgO and anion exchange resins. This catalyst also acts as a heterogeneous catalyst for the epoxidation of electron‐deficient olefins with hydrogen peroxide. Further, the catalyst/product(s) separation can be easily carried out by the simple filtration (or centrifugation) and the reaction is immediately stopped by the removal of the solid catalyst, suggesting that the nature of the observed catalysis is truly heterogeneous.