40326-25-8Relevant academic research and scientific papers
Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis
Sato, Eisuke,Fujii, Mayu,Tanaka, Hiroki,Mitsudo, Koichi,Kondo, Masaru,Takizawa, Shinobu,Sasai, Hiroaki,Washio, Takeshi,Ishikawa, Kazunori,Suga, Seiji
supporting information, p. 16035 - 16044 (2021/09/02)
Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.
Germyliumylidene: A Versatile Low Valent Group 14 Catalyst
Sarkar, Debotra,Dutta, Sayan,Weetman, Catherine,Schubert, Emeric,Koley, Debasis,Inoue, Shigeyoshi
supporting information, p. 13072 - 13078 (2021/08/09)
Bis-NHC stabilized germyliumylidenes [RGe(NHC)2]+ are typically Lewis basic (LB) in nature, owing to their lone pair and coordination of two NHCs to the vacant p-orbitals of the germanium center. However, they can also show Lewis acidity (LA) via Ge?CNHC σ* orbital. Utilizing this unique electronic feature, we report the first example of bis-NHC-stabilized germyliumylidene [MesTerGe(NHC)2]Cl (1), (MesTer=2,6-(2,4,6-Me3C6H2)2C6H3; NHC= IMe4=1,3,4,5-tetramethylimidazol-2-ylidene) catalyzed reduction of CO2 with amines and arylsilane, which proceeds via its Lewis basic nature. In contrast, the Lewis acid nature of 1 is utilized in the catalyzed hydroboration and cyanosilylation of carbonyls, thus highlighting the versatile ambiphilic nature of bis-NHC stabilized germyliumylidenes.
n-Butyllithium as a highly efficient precatalyst for cyanosilylation of aldehydes and ketones
Kang, Zihan,Wang, Yuhong,Xu, Xiaojuan,Xue, Mingqiang,Zhang, Wenxuan,Zhou, Shuai,Zhu, Xu
supporting information, p. 7432 - 7437 (2021/09/07)
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
A novel yttrium-based metal-organic framework for the efficient solvent-free catalytic synthesis of cyanohydrin silyl ethers
Cepeda, Javier,Echenique-Errandonea, Estitxu,Fernández, Ignacio,Pérez, Juana M.,Rodríguez-Diéguez, Antonio,Rojas, Sara,Seco, José M.
supporting information, p. 11720 - 11724 (2021/09/06)
A new porous metal-organic framework (MOF) with the chemical formula [Y5L6(OH)3(DMF)3]·5H2O (1) (where L = 3-amino-4-hydroxybenzoate) has been prepared by a solvothermal procedure. The structural char
Synthesis of cyanooxovanadate and cyanosilylation of ketones
Hayashi, Yoshihito,Kawabata, Hiroko,Kikukawa, Yuji
, p. 31688 - 31692 (2021/11/30)
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 [
[Mes-B-TMP]+borinium cation initiated cyanosilylation and catalysed hydrosilylation of ketones and aldehydes
Chen, Po-Han,Chiu, Ching-Wen,Hsu, Ching-Pei,Liu, Yi-Hung,Tseng, Hsi-Ching
supporting information, p. 13732 - 13735 (2021/12/27)
Two aryl amino borinium cations derived from Cl(Mes)B-NR2(NR2= TMP, HMDS) faced divergent outcomes. As the HMDS-substituted one underwent methyl migration from silicon to boron transforming the putative borinium ion to a silylium ion, [Mes-B-TMP]+can initiate cyanosilylation and catalyse hydrosilylation of ketones and aldehydes.
Ultrathin Near-Infrared Light Activated Nano-Hotplate Catalyst
Wu, Xiangyang,Yeow, Edwin K. L.
, (2020/09/09)
A combined photothermal-catalytic system that contains a single active element, without using different entities for separate roles (catalytic vs photothermal), is designed here for efficient catalytic reactions. Herein, ultrathin (sub-6 nm) rectangular-l
Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade
Garnes-Portolés, Francisco,Leyva-Pérez, Antonio,Rivero-Crespo, Miguel ángel
, p. 21 - 28 (2020/10/21)
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
Catalytic Transfer Hydration of Cyanohydrins to α-Hydroxyamides
Kanda, Tomoya,Naraoka, Asuka,Naka, Hiroshi
supporting information, p. 825 - 830 (2019/01/14)
We report the palladium(II)-catalyzed transfer hydration of cyanohydrins to α-hydroxyamides by using carboxamides as water donors. This method enables selective hydration of various aldehyde- and ketone-derived cyanohydrins to afford α-mono- and α,α-disubstituted-α-hydroxyamides, respectively, under mild conditions (50 °C, 10 min). The direct conversion of fenofibrate, a drug bearing a benzophenone moiety, into a functionalized α,α-diaryl-α-hydroxyamide was achieved by means of a hydrocyanation-transfer hydration sequence. Preliminary kinetic studies and the synthesis of a site-specifically 18O-labeled α-hydroxyamide demonstrated the carbonyl oxygen transfer from the carboxamide reagent into the α-hydroxyamide product.
Beyond Hydrofunctionalisation: A Well-Defined Calcium Compound Catalysed Mild and Efficient Carbonyl Cyanosilylation
Yadav, Sandeep,Dixit, Ruchi,Vanka, Kumar,Sen, Sakya S.
supporting information, p. 1269 - 1273 (2018/02/06)
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
