Activation of trimethylsilyl cyanide and mechanistic investigation for facile cyanosilylation by solid acid catalysts under mild and solvent-free conditions

被引：22
作者：
Thirupathi, Boningari [1 ]
Patil, Meghshyam K. [1 ]
Reddy, Benjaram M. [1 ]
机构：
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500607, Andhra Pradesh, India
来源：
APPLIED CATALYSIS A-GENERAL | 2010年 / 384卷 / 1-2期
关键词：
Cyanosilylation; Sulfated-zirconia; Mechanistic investigations; Solid acids; Solvent-free synthesis; SULFATED ZIRCONIA; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE CYANOSILYLATION; SYNTHETIC APPLICATIONS; ALPHA-AMINONITRILES; CARBONYL-COMPOUNDS; LEWIS-ACID; STATE NMR; KETONES; ALDEHYDES;
D O I：
10.1016/j.apcata.2010.06.019
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Sulfated-zirconia is found to be a highly efficient heterogeneous solid catalyst in activating trimethylslyl cyanide (TMSCN) for facile cyanosilylation of aldehydes. A unifying explanation is provided for the cyanosilylation reactions. The unique role of sulfated-zirconia consists of rendering cyanide anions from TMSCN to C=O of aldehydes and providing the corresponding cyanohydrin silyl ethers in quantitative yields under mild and solvent-free conditions. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码：147 / 153
页数：7
相关论文
共 52 条
  • [21] IN MS, 1993, CYANOHYDRINS ENCY CH, V7, P821
  • [22] Kadam ST, 2008, B KOREAN CHEM SOC, V29, P1320
  • [23] A highly efficient and recyclable silica-based scandium(III) interphase catalyst for cyanosilylation of carbonyl compounds
    Karimi, B
    Ma'Mani, L
    [J]. ORGANIC LETTERS, 2004, 6 (26) : 4813 - 4815
  • [24] Polymer scandium-catalyzed three-component reactions leading to diverse amino ketone, amino ester, and amino nitrile derivatives
    Kobayashi, S
    Nagayama, S
    Busujima, T
    [J]. TETRAHEDRON LETTERS, 1996, 37 (51) : 9221 - 9224
  • [25] Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones
    Kurono, N
    Yamaguchi, M
    Suzuki, K
    Ohkuma, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) : 6530 - 6532
  • [26] Oxidative activation of n-butane on sulfated zirconia
    Li, XB
    Nagaoka, K
    Simon, LJ
    Olindo, R
    Lercher, JA
    Hofmann, A
    Sauer, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16159 - 16166
  • [27] Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt
    Liu, XH
    Qin, B
    Zhou, X
    He, B
    Feng, XM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) : 12224 - 12225
  • [28] Methane carbonylation with CO on sulfated zirconia: Evidence from solid-state NMR for the selective formation of acetic acid
    Luzgin, Mikhail V.
    Rogov, Vladimir A.
    Kotsarenko, Nina S.
    Shmachkova, Vera P.
    Stepanov, Alexander G.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (28) : 10624 - 10629
  • [29] Measurement of heat of argon adsorption for the evaluation of relative acid strength of some sulfated metal oxides and H-type zeolites
    Matsuhashi, H
    Tanaka, T
    Arata, K
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2001, 105 (40): : 9669 - 9671
  • [30] Characterization of sulfated zirconia prepared using reference catalysts and application to several model reactions
    Matsuhashi, Hiromi
    Nakamura, Hideo
    Ishihara, Tatsumi
    Iwamoto, Shinji
    Kamiya, Yuichi
    Kobayashi, Junya
    Kubota, Yoshihiro
    Yamada, Takashi
    Matsuda, Takeshi
    Matsushita, Koichi
    Nakai, Kazuyuki
    Nishiguchi, Hiroyasu
    Ogura, Masaru
    Okazaki, Noriyasu
    Sato, Satoshi
    Shimizu, Ken-ichi
    Shishido, Tetsuya
    Yamazoe, Seiji
    Takeguchi, Tatsuya
    Tomishige, Keiichi
    Yamashita, Hiromi
    Niwa, Miki
    Katada, Naonobu
    [J]. APPLIED CATALYSIS A-GENERAL, 2009, 360 (01) : 89 - 97
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