159015-72-2Relevant articles and documents
Oxyfunctionalization reactions by perfluoro cis-2,3-dialkyloxaziridines. Enantioselective conversion of silanes into silanols
Cavicchioli, Marcello,Montanari, Vittorio,Resnati, Giuseppe
, p. 6329 - 6330 (1994)
Perfluoro cis-2,3-dialkyloxaziridine 2 is shown to perform the oxyfunctionalization of silanes 1 under very mild conditions to give silanols and silanediols 3 in high chemical yields and complete enantioselectivity.
Efficient heterogeneous oxidation of organosilanes to silanols catalysed by a hydroxyapatite-bound Ru complex in the presence of water and molecular oxygen
Mori, Kohsuke,Tano, Makoto,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 1536 - 1538 (2002)
RuHAP is a highly selective and reusable catalyst for the oxidation of a wide variety of organosilanes to the corresponding silanols in the presence of water and molecular oxygen.
Organocatalytic oxidation of organosilanes to silanols
Limnios, Dimitris,Kokotos, Christoforos G.
, p. 2239 - 2243 (2013)
The oxidation of organosilanes to silanols constitutes an attractive transformation for both industry and academia. Bypassing the need for stoichiometric oxidants or precious metal catalytic complexes, the first organocatalytic oxidation of silanes has been accomplished. Catalytic amounts of 2,2,2-trifluoroacetophenone, in combination with the green oxidant H 2O2, lead to excellent to quantitative yields in a short reaction time. A variety of alkyl, aryl, alkenyl, and alkynyl substituents can be tolerated, providing an easy, cheap, efficient, and practical solution to a highly desirable transformation.
Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations
Liang, Hao,Wang, Lu-Jun,Ji, Yun-Xing,Wang, Han,Zhang, Bo
supporting information, p. 1839 - 1844 (2020/12/01)
The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen-atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional-group compatibility, and it is applicable to late-stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H2O.
Selective Manganese-Catalyzed Oxidation of Hydrosilanes to Silanols under Neutral Reaction Conditions
Wang, Kaikai,Zhou, Jimei,Jiang, Yuting,Zhang, Miaomiao,Wang, Chao,Xue, Dong,Tang, Weijun,Sun, Huamin,Xiao, Jianliang,Li, Chaoqun
supporting information, p. 6380 - 6384 (2019/05/06)
The first manganese-catalyzed oxidation of organosilanes to silanols with H2O2 under neutral reaction conditions has been accomplished. A variety of organosilanes with alkyl, aryl, alknyl, and heterocyclic substituents were tolerated, as well as sterically hindered organosilanes. The oxidation appears to proceed by a concerted process involving a manganese hydroperoxide species. Featuring mild reaction conditions, fast oxidation, and no waste byproducts, the protocol allows a low-cost, eco-benign synthesis of both silanols and silanediols.
Single-Site AuI Catalyst for Silane Oxidation with Water
Chen, Zheng,Zhang, Qi,Chen, Wenxing,Dong, Juncai,Yao, Hurong,Zhang, Xiangbo,Tong, Xuanjue,Wang, Dingsheng,Peng, Qing,Chen, Chen,He, Wei,Li, Yadong
, (2017/12/18)
Single-site Au anchored on mpg-C3N4 (519 ppm Au loading) is developed as a highly active, selective, and stable catalyst for the oxidation of silanes with water with a turnover frequency as high as 50 200 h?1, far exceeding most known catalysts based on total gold content. Other hydrosilanes bearing unsaturated functional groups also lead to corresponding silanols under mild reaction conditions without formation of any side products in good or excellent yields. The spherical aberration correction electron microscopy and extended X-ray absorption fine structure measurements both confirm the atomic dispersion of Au atoms stabilized by mpg-C3N4. The coordination of the catalytically active AuI by three nitrogen or carbon atoms in the tri-s-triazine repeating units not only prevents the Au atoms from aggregation, but also renders the surface AuI highly active, which is completely different than homogeneous AuI species.
Metal-free visible-light-mediated aerobic oxidation of silanes to silanols
Wang, Jing,Li, Bin,Liu, Li-Chuan,Jiang, Chenran,He, Tao,He, Wei
, p. 1594 - 1599 (2018/08/22)
Oxidation of silanes into silanols using water/air has attracted considerable attention. The known methods with no exception required a metal catalyst. Herein we report the first metal-free method: 2 mol% Rose Bengal as the catalyst, air (O2) as the oxidant, water as the additive and under visible light irradiation. While this method produces various silanols in a simple, cost-effective, efficient (92%–99% yields) and scalable fashion, its reaction mechanism is very different than the reported ones associated with metal catalysis.
A method for catalytic synthesis of silanol
-
Paragraph 0017; 0043; 0044, (2017/07/12)
The invention discloses a method for catalytically synthesizing silanol and relates to the fields of organic chemicals and fine chemicals. The method is essentially a transition metal catalyzed organic synthesis reaction. In the method, the raw materials comprise organosilane and a clean oxidant, a used catalyst is inexpensive copper salt, the raw material is heated and stirred to react without a solvent so as to rapidly produce silanol at a moderate temperature. By adopting the method, the reaction time is 3-12 hours. The mole ratio of the organosilane to the clean oxidant is 1:(1-5), the copper salt as the catalyst accounts for 1-10mol% of the mole number of the organosilane, the raw materials react at a temperature of 50-80 DEG C, and then the silanol can be greatly yielded after simple posttreatment. The oxidant used in the method is safe and nontoxic, and the catalyst used in the method is cheap and easily available. The method disclosed by the invention is a very simple and practical method for synthesizing silanol.
Nanostructured materials as catalysts: Nanoporous-gold-catalyzed oxidation of organosilanes with water
Asao, Naoki,Ishikawa, Yoshifumi,Hatakeyama, Naoya,Menggenbateer,Yamamoto, Yoshinori,Chen, Mingwei,Zhang, Wei,Inoue, Akihisa
experimental part, p. 10093 - 10095 (2011/03/16)
Pores to the fore: Nanoporous gold shows a remarkable catalytic activity for the oxidation of organosilane compounds with water. The catalyst is easily recoverable and can be reused several times without leaching and loss of activity. Copyright
Highly selective oxidation of organosilanes to silanols with hydrogen peroxide catalyzed by a lacunary polyoxotungstate
Ishimoto, Ryo,Kamata, Keigo,Mizuno, Noritaka
supporting information; experimental part, p. 8900 - 8904 (2010/01/16)
Silanol synthesis: Divacant lacunary polyoxotungstate (nBu4N+)4[g- SiW10O34(H2O)2] (I) is an efficient homogeneous catalyst for highly selective oxidation of organosilanes to silanols with 30/60% aqueous H2O2. Various kinds of silanes 1 containing aryl, alkyl, alkenyl, alkynyl and alkoxy groups are chemoselectively converted into the corresponding silanols 2 in high yields with only one equivalent of aqueous H2O2 with respect to the substrate.
