- n-Butyllithium as a highly efficient precatalyst for cyanosilylation of aldehydes and ketones
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A highly efficient cyanosilylation protocol mediated by the easily availablen-BuLi with a wide range of aldehydes and ketones was developed. This protocol features excellent yields with very lown-BuLi loadings (0.01-0.05 mol%) at room temperature, solvent
- Kang, Zihan,Wang, Yuhong,Xu, Xiaojuan,Xue, Mingqiang,Zhang, Wenxuan,Zhou, Shuai,Zhu, Xu
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supporting information
p. 7432 - 7437
(2021/09/07)
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- Conjugated Bis-Guanidines (CBGs) as β-Diketimine Analogues: Synthesis, Characterization of CBGs/Their Lithium Salts and CBG Li Catalyzed Addition of B?H and TMSCN to Carbonyls
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Herein, we report a range of conjugated bis-guanidines (CBGs) L [L={(ArHN)(ArHN)C=N?C=(NAr)(NHAr)}; Ar=2, 6-Me2 - C6H3, (1), 2, 4, 6-Me3?C6H2, (2), 2, 6-Et2?C6H3
- Peddarao, Thota,Baishya, Ashim,Sarkar, Nabin,Acharya, Rudresh,Nembenna, Sharanappa
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p. 2034 - 2046
(2021/05/27)
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- Synthesis of cyanooxovanadate and cyanosilylation of ketones
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The cyanosilylation was performed by using metavanadate catalysts, and in situ measurements revealed the formation of [VO2(CN)3]2- and [VO4TMS2]- under reaction conditions. The reaction of [VO2(CN)3]2-, trimethylsilyl cyanide (TMSCN), and water afforded [
- Hayashi, Yoshihito,Kawabata, Hiroko,Kikukawa, Yuji
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p. 31688 - 31692
(2021/11/30)
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- Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade
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The cyanosilylation of carbonyl compounds is a fundamental reaction in organic synthesis, to give cyanohydrins. Ketones are particularly reluctant to cyanosilane addition and require the action of a catalyst, and despite many soluble Br?nsted and Lewis ac
- Garnes-Portolés, Francisco,Leyva-Pérez, Antonio,Rivero-Crespo, Miguel ángel
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- A micro-environment tuning approach for enhancing the catalytic capabilities of lanthanide containing polyoxometalate in the cyanosilylation of ketones
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The as-synthesized (TBA)8H5[Nd(SiW11O39)2] manifested high catalytic activity for cyanosilylation of ketones, and its catalytic activity could be improved further through rational design of the reacti
- Li, Sang-Hao,Lin, Ming-Yuan,Nie, Yan-Mei,Yan, Jun
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supporting information
p. 3809 - 3812
(2020/04/10)
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- Application of n-butyllithium in catalyzing cyanosilylation reaction of ketone and silane
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The invention discloses an application of n-butyllithium in catalyzing cyanosilylation reaction of ketone and silane. The n-butyllithium has high catalytic activity, low catalyst dosage and good substrate application range. After n-butyllithium, ketone an
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Paragraph 0024
(2020/07/13)
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- Pickering emulsion droplets hosting ionic liquid catalysts for continuous-flow cyanosilylation reaction
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An IL-catalyzed cyanosilylation reaction is an important route for synthesis of many fine chemicals, but it is currently conducted in a batch manner. Herein, we have developed a novel method to "immobilize" IL catalysts for continuous-flow reaction based
- Meng, Zhixin,Zhang, Ming,Yang, Hengquan
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p. 627 - 633
(2019/02/14)
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- Syntheses, Structures, and Catalytic Activities of the Anionic Heterobimetallic Rare-Earth Metal Complexes Supported by Pyrrolyl-Substituted 1,2-Diimino Ligands
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A series of the anionic heterobimetallic rare-earth metal complexes supported by trans- or chiral pyrrolyl-substituted 1,2-diimino ligands were synthesized in good yields via reactions of [(Me3Si)2N]3RE(μ-Cl)Li(THF)3
- Wang, Wei,Wang, Xiaojia,Zhou, Shuangliu,Xu, Xiaolong,Du, Jun,Zhang, Lijun,Mu, Xiaolong,Wei, Yun,Zhu, Xiancui,Wang, Shaowu
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supporting information
p. 10390 - 10400
(2018/08/28)
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- Cyanosilylation reaction method using hydroboron to catalyze ketone
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The invention relates to the field of organic chemistry, aiming at solving the problems that the existing ketone-catalyzing cyanosilylation reaction has the defects of complicated catalyst structure,high preparation cost and more application limitations,
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Paragraph 0033
(2018/05/03)
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- Beyond Hydrofunctionalisation: A Well-Defined Calcium Compound Catalysed Mild and Efficient Carbonyl Cyanosilylation
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Organocalcium compounds have been reported as efficient catalysts for various transformations, for cases in which one of the substrates contained an E?H (E=B, N, Si, P) bond. Here, we look at the possibility of employing an organocalcium compound for a tr
- Yadav, Sandeep,Dixit, Ruchi,Vanka, Kumar,Sen, Sakya S.
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supporting information
p. 1269 - 1273
(2018/02/06)
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- Exploring physical and chemical properties in new multifunctional indium-, bismuth-, and zinc-based 1D and 2D coordination polymers
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Main group element coordination polymers (MGE-CPs) are important compounds for the development of multifunctional materials. However, there has been a shortage of studies regarding their structural, optical, catalytic, mechanical, and antibacterial proper
- Gomez,D'Vries,Lionello,Aguirre-Díaz,Spinosa,Costa,Fuertes,Pizarro,Kaczmarek,Ellena,Rozes,Iglesias,Van Deun,Sanchez,Monge,Soler-Illia
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p. 1808 - 1818
(2018/02/17)
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- Easily accessible lithium compound catalyzed mild and facile hydroboration and cyanosilylation of aldehydes and ketones
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Simple and readily accessible lithium compounds such as 2,6-di-tert-butyl phenolate lithium (1a), 1,1′ dilithioferrocene (1b) and nacnac lithium (1c) are found to be efficient single site catalysts for hydroboration of a range of aldehydes and ketones wit
- Bisai, Milan Kumar,Das, Tamal,Vanka, Kumar,Sen, Sakya S.
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supporting information
p. 6843 - 6846
(2018/06/26)
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- Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds
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We report here reactions between the N-adamantyliminopyrolyl ligand 2-(AdNCH)-C4H3NH (L-H) and alkali metal hexamethyldisilazides [MN(SiMe3)2] (M = Li, Na and K) to afford the dimeric [{2-(AdNCH)-C4H
- Harinath, Adimulam,Bhattacharjee, Jayeeta,Nayek, Hari Pada,Panda, Tarun K.
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supporting information
p. 12613 - 12622
(2018/09/27)
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- Chiral rare-earth metal complexes with a tridentate amido-fluorenyl ligand: Syntheses, structures and catalytic performance
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The complexes of rare-earth metals (Y, La, Sm and Lu) with a chiral tridentate amido-fluorenyl ligand were synthesized and characterized. These complexes demonstrated high efficiency in catalyzing both the intramolecular hydroamination of non-activated ol
- Chai, Zhuo,Wang, Yemei,Tang, Mujun,Mu, Xiaolong,Hou, Jinsong,Yang, Gaosheng
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p. 236 - 241
(2017/07/04)
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- Toward understanding the structure-catalyst activity relationship of new indium MOFs as catalysts for solvent-free ketone cyanosilylation
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Four new indium metal-organic frameworks, MOFs, namely [In2(hfipbb)3(1,10-phen)2]·2H2O (InPF-12), [In2(hfipbb)3(2,2′-bipy)2]·2H2O (InPF-13), [In2(hfipbb)su
- Aguirre-Daz, Lina Mara,Iglesias, Marta,Snejko, Natalia,Gutirrez-Puebla, Enrique,Monge, M. ngeles
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p. 7058 - 7065
(2015/01/30)
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- An Aluminum Hydride That Functions like a Transition-Metal Catalyst
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The reaction of [LAlH2] (L=HC(CMeNAr)2, Ar=2,6-iPr2C6H3) with MeOTf (Tf=SO2CF3) resulted in the formation of [LAlH(OTf)] (1) in high yield. The triflate substituent in 1 increases the positive charge at the aluminum center, which implies that 1 has a strong Lewis acidic character. The excellent catalytic activity of 1 for the hydroboration of organic compounds with carbonyl groups was investigated. Furthermore, it was shown that 1 effectively initiates the addition reaction of trimethylsilyl cyanide (TMSCN) to both aldehydes and ketones. Quantum mechanical calculations were carried out to explore the reaction mechanism.
- Yang, Zhi,Zhong, Mingdong,Ma, Xiaoli,De, Susmita,Anusha, Chakkittakandiyil,Parameswaran, Pattiyil,Roesky, Herbert W.
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supporting information
p. 10225 - 10229
(2015/09/01)
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- Porous barium-organic frameworks with highly efficient catalytic capacity and fluorescence sensing ability
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The current study describes the first barium-organic framework with permanent porosity, efficient catalytic capacity, and highly selective luminescence sensing of DMSO molecules and metal ions. Single-crystal-to-single-crystal transformations (from comple
- Liu, Fuling,Xu, Yuwen,Zhao, Lianming,Zhang, Liangliang,Guo, Wenyue,Wang, Rongming,Sun, Daofeng
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supporting information
p. 21545 - 21552
(2015/11/10)
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- Indium metal-organic frameworks as catalysts in solvent-free cyanosilylation reaction
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Two new Indium MOFs with the bending multicarboxylate ligand H 2dpmda as a linker and different N-donor ancillary ligands were obtained; the two compounds are isoreticular with 2D-hcb uninodal 3-connected nets. Comparison of their activity in c
- Aguirre-Diaz, Lina Maria,Iglesias, Marta,Snejko, Natalia,Gutierrez-Puebla, Enrique,Monge, M. Angeles
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p. 9562 - 9571
(2013/11/19)
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- Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls
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Here we report a sustainable protocol for the cyanosilylation of carbonyl compounds 1a-g and 3a-m using trimethylsilyl cyanide and triphenylphosphine supported on polystyrene as a catalyst under solvent-free conditions. It has been shown that a small amou
- Strappaveccia, Giacomo,Lanari, Daniela,Gelman, Dmitri,Pizzo, Ferdinando,Rosati, Ornelio,Curini, Massimo,Vaccaro, Luigi
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p. 199 - 204
(2013/02/23)
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- Cyanosilylation of carbonyl compounds with trimethylsilyl cyanide catalyzed by an yttrium-pillared silicotungstate dimer
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An yttrium-pillared silicotungstate dimer (see picture) catalyzes the cyanosilylation of structurally diverse ketones and aldehydes with trimethylsilyl cyanide (TMSCN). The reactions proceed selectively and afford the corresponding cyanohydrin trimethylsi
- Kikukawa, Yuji,Suzuki, Kosuke,Sugawa, Midori,Hirano, Tomohisa,Kamata, Keigo,Yamaguchi, Kazuya,Mizuno, Noritaka
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supporting information; experimental part
p. 3686 - 3690
(2012/05/20)
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- Strategic design and refinement of Lewis acid-base catalysis by rare-earth-metal-containing polyoxometalates
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Efficient polyoxometalate (POM)-based Lewis acid-base catalysts of the rare-earth-metal-containing POMs (TBA6RE-POM, RE = Y3+, Nd3+, Eu3+, Gd3+, Tb3+, or Dy 3+) were designed and
- Suzuki, Kosuke,Sugawa, Midori,Kikukawa, Yuji,Kamata, Keigo,Yamaguchi, Kazuya,Mizuno, Noritaka
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experimental part
p. 6953 - 6961
(2012/08/28)
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- Efficient, rapid and solvent-free cyanosilylation of aldehydes and ketones catalyzed by SbCl3
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Antimony trichloride(SbCl3) was demonstrated to be an effective catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the correspon
- Pourmousavi,Salahshornia
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experimental part
p. 1575 - 1578
(2011/12/15)
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- Synthesis of chiral α-ethylphenylamine salts of tartaric acid and novel application to cyanosilylation of prochiral ketones
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Chiral α-ethylphenylamine tartaric acid salts were synthesized from a-ethylphenylamine by direct reaction with chiral tartaric acid. The crystal structure of S-(-)-αethylphenylamine-( 2R,3R)-(-)-dihydroxybutanedioic acid was determined. The crystal is mon
- Mei, Luo,Jie, Sun,Ying, Jiang
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experimental part
p. 227 - 236
(2011/10/18)
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- Alkali salt of L-proline as an efficient and practical catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions
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The alkali salt of L-proline was demonstrated to be an efficient and practical catalyst for the cyanosilylation of a wide variety of simple and functionalized carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the corresponding cyanohydrins in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Shen, Zhi-Liang,Ji, Shun-Jun
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experimental part
p. 775 - 791
(2009/08/08)
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- Gold(III)-catalyzed cyanosilylation of ketones and aldehydes
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Gold(III) chloride was found to be a highly efficient catalyst for the cyanosilylation of various ketones and aldehydes. The reactions were complete within 30 minutes at room temperature in the presence of only one mol% gold(III) chloride, yielding the co
- Woo, Kyung Cho,Sung, Min Kang,Medda, Amiya K.,Lee, Jungkyu K.,Choi, Insung S.,Lee, Hee-Seung
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p. 507 - 510
(2008/12/21)
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- Cyanosilylation of aldehydes and ketones catalyzed by nanocrystalline magnesium oxide
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Cyanosilylation of various aldehydes and ketones with TMSCN proceeded smoothly under mild conditions to give the corresponding cyanohydrin trimethylsilyl ethers in the presence of nanocrystalline magnesium oxide. The cyanohydrin trimethylsilyl ethers of aldehydes produced cyanohydrins in good to high yields on treatment with 2 N HCl. 29Si NMR spectral evidence proved that the reaction proceeds through the hypervalent silicate species by coordination to O2-/O- (Lewis basic site) of nanocrystalline magnesium oxide. Copyright Taylor & Francis Group, LLC.
- Lakshmi Kantam,Mahendar, Koosam,Sreedhar, Bojja,Vijay Kumar,Choudary
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experimental part
p. 3919 - 3936
(2009/04/11)
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- Fe(Cp)2PF6: An efficient catalyst for cyanosilylation of carbonyl compounds under solvent free condition
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An efficient method for the addition of trimethylsilyl cyanide (TMSCN) to various aldehydes and ketones has been described using Fe(Cp)2PF6 (2.5 mol%) as a catalyst under solvent free condition. Excellent yields of trimethylsilylethe
- Khan, Noor-ul H.,Agrawal, Santosh,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Singh, Surendra,Jasra, Raksh V.
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p. 4361 - 4366
(2008/02/13)
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- Catalytic cyanosilylation of ketones using organic catalyst 1,1,3,3-tetramethylguanidine
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1,1,3,3-Tetramethylguanidine acts as a highly effective catalyst for cyanosilylation of various ketones and aldehydes to the corresponding cyanohydrin trimethylsilyl ethers in up to 99% yield. The reaction proceeds smoothly with 0.1 mol % catalyst loading
- Wang, Lijia,Huang, Xiao,Jiang, Jun,Liu, Xiaohua,Feng, Xiaoming
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p. 1581 - 1584
(2007/10/03)
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- Cyanosilylation of prochiral ketones catalyzed by lanthanide complexes
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A new series of silylene-bridged rare-earth complexes involving fluorenyl are shown to be the very efficient Lewis acid catalysts, giving some cyano trimethylsilyl ethers of ketones in >99% yields. Copyright Taylor & Francis, Inc.
- Mei, Luo,Zhu, Ma Huai
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p. 2615 - 2623
(2007/10/03)
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- Cyanosilylation of ketones catalyzed by quaternary ammonium salt and N-oxide
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Dibenzyldimethyl ammonium bromide and triethanolamine N-oxide catalyze the formation of cyanohydrin trimethylsilyl ethers of ketones in 80-99% yield.
- Zhou, Hui,Chen, Fu-Xue,Qin, Bo,Feng, Xiaoming,Zhang, Guolin
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p. 1077 - 1079
(2007/10/03)
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- Highly efficient double-activation catalysts for the synthesis of ketone cyanohydrins
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Tertiary cyanohydrin trimethylsilyl ethers were synthesized in excellent chemical yields by using salen-Al complex (0.25 mol%) and N-oxide (0.5 mol%) without solvent at ambient temperature. The relationship between the ligand structure and catalyst effici
- Chen, Fu-Xue,Liu, Xiaohua,Qin, Bo,Zhou, Hui,Feng, Xiaoming,Zhang, Guolin
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p. 2266 - 2272
(2007/10/03)
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- Asymmetric Cyanosilylation of Ketones Catalyzed by Bifunctional Chiral N-Oxide Titanium Complex Catalysts
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A new bifunctional catalytic system based on chiral N-oxide titanium complexes has been used for the asymmetric cyanosilylation of ketones. Screening of a variety of chiral N-oxide metal complexes resulted in (1R,2S)-1-(2'-pyridylmethyl)-2-(diphenylhydroxymethyl)pyrrolidine N-oxide titanium complex, which gave O-TMS cyanohydrins in good yields with enantiometric excesses of up to 69 percent. A catalytic cycle based on experimental phenomena and studies was proposed to explain the origin of the asymmetric induction.
- Shen, Yongcun,Feng, Xiaoming,Li, Yan,Zhang, Guolin,Jiang, Yaozhong
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p. 129 - 137
(2007/10/03)
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- Inorganic/organic salts as heterogeneous basic catalysts for cyanosilylation of carbonyl compounds
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The addition of TMSCN to carbonyl compounds catalyzed by K 2CO3 as heterogeneous catalyst gave the corresponding cyanohydrin trimethylsilyl ethers from 20 minutes to 24 hours with 62% to 99% yields without solvent at room temperature
- He, Bin,Li, Yan,Feng, Xiaoming,Zhang, Guolin
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p. 1776 - 1778
(2007/10/03)
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- Highly Efficient Silylcyanation of Ketones by a Catalytic Double Activation Method Using Lewis Acid and N-Oxide Catalysts
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An efficient protocol for addition of TMSCN to ketones by employing 3 mol percent achiral Schiff base-Ti(IV) complex as the Lewis acid and 3 mol percent N-oxide as the Lewis base in a manner of double activation was described. Aromatic, aliphatic, cyclic,
- Chen, Fuxue,Feng, Xiaoming,Qin, Bo,Zhang, Guolin,Jiang, Yaozhong
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p. 558 - 560
(2007/10/03)
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- A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid-Lewis base bifunctional catalyst
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A new family of bifunctional catalysts (N-oxides-Ti(OiPr)4 (2:1)) containing a Lewis acid and a Lewis base was developed and applied to the catalytic cyanosilylation of ketones. Utilizing rac((1R,2S) and (1S,2R))-1-(2′-pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide-titanium (2:1) complex and N-benzyl-diethanolamine N-oxide-titanium (2:1) complex as catalysts, the cyanosilylation products were obtained in 42-97% yield. Based on experimental phenomena and kinetic studies, a catalytic cycle was proposed to explain the remarkable activities of these catalysts. Investigations indicated that rac((1R,2S) and (1S,2R))-1-(2′-pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide-titanium (2:1) complex and N-benzyl-diethanolamine N-oxide-titanium (2:1) complex should promote the reaction via a dual activation of the ketone by the titanium and TMSCN by the N-oxide.
- Shen, Yongcun,Feng, Xiaoming,Li, Yan,Zhang, Guolin,Jiang, Yaozhong
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p. 5667 - 5675
(2007/10/03)
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- A mild and efficient cyanosilylation of ketones using in situ generated n-oxides-ti(iPrO)4 complexes as catalysts
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The addition of TMSCN to ketones catalyzed by complex of racemic N-(2′-pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide (rac-1) or N-benzyl-N,N-dihydroxyethylamine N-oxide and Ti(iPrO)4 affords the racemic O-TMS cyanohydrins in good to excellent isolated yields (up to 97%) under mild reaction conditions.
- Shen, Yongcun,Feng, Xiaoming,Li, Yan,Zhang, Guolin,Jiang, Yaozhong
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p. 793 - 795
(2007/10/03)
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- Addition of trimethylsilyl cyanide to aromatic ketones promoted by organic solutions of lithium salts
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Cyanosilylation of aromatic ketones is strongly promoted in organic solutions of specific lithium salts (perchlorate and tetrafluoroborate). Acetonitrile solutions of LiBF4 are safe and efficient media for this reaction.
- Jenner, Gerard
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p. 491 - 494
(2007/10/03)
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- Calcined MgAlCO3-HT catalysed cyanosilylation of carbonyl compounds and nucleophilic ring opening of oxiranes using TMSCN
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Nucleophilic addition of TMSCN to carbonyl compounds is found to be catalysed efficiently using hydrotalcite as a solid base. The catalyst is also found to be active in the nucleophilic ring opening of oxiranes giving high regioselectivity.
- Choudary,Narender,Bhuma
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p. 2829 - 2836
(2007/10/02)
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