139526-41-3Relevant academic research and scientific papers
Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: Dioxygen initiation
Postigo, Al,Nudelman, Norma Sbarbati
, p. 910 - 914 (2010)
The relevance of radical initiation methodologies for the classical hydrosilylation reactions of organic compounds bearing C-C multiple bonds is due to the need to come up with newer and more efficient methods to effect this reaction, on account of its ap
A mild and efficient Si (111) surface modification via hydrosilylation of activated alkynes
Liu, Yang,Yamazaki, Shoko,Yamabe, Shinichi,Nakato, Yoshihiro
, p. 4906 - 4913 (2005)
A new Si surface modification with organic groups via hydrosilylation at room temperature is reported. A hydrogen-terminated Si (111) surface was reacted with activated alkynes such as propiolate esters, propiolic acid, but-3-yne-2-one, propiolonitrile and phenylacetylene at room temperature for 24-40 h to give modified surfaces. The coverage ratio was estimated to be 31-56% by XPS analysis. This surface modification method is mild, highly efficient and procedurally simple. The novel surfaces modified with various organic functional groups are expected to have interesting utilities. The Royal Society of Chemistry 2005.
Development of a Radical Silylzincation of (Het)Aryl-Substituted Alkynes and Computational Insights into the Origin of the trans-Stereoselectivity
Romain, Elise,de la Vega-Hernández, Karen,Guégan, Frédéric,Sanz García, Juan,Fopp, Carolin,Chemla, Fabrice,Ferreira, Franck,Gerard, Hélène,Jackowski, Olivier,Halbert, Stéphanie,Oestreich, Martin,Perez-Luna, Alejandro
, p. 2634 - 2647 (2021/03/30)
Aryl- and hetaryl-substituted acetylenes undergo regio- and stereoselective silylzincation by reaction with [(Me3Si)3Si]2Zn in the presence of Et2Zn (10–110 mol%) as additive. The distinctive feature of this addition across the C?C triple bond is its trans stereoselectivity. The radical nature of the silylzincation process is supported by diagnostic experiments and DFT calculations, which also corroborate the role played by steric effects to obtain that stereoselectivity. The procedure can be combined in one-pot with the copper(I)-mediated electrophilic substitution of the C(sp2)?Zn bond, with retention of the double bond geometry. This makes it valuable for the synthesis of stereodefined di- and trisubstituted vinylsilanes. (Figure presented.).
Radical Hydrosilylation of Alkynes Catalyzed by Eosin y and Thiol under Visible Light Irradiation
Zhu, Jing,Cui, Wei-Chen,Wang, Shaozhong,Yao, Zhu-Jun
supporting information, p. 3174 - 3178 (2018/06/11)
A visible light-promoted hydrosilylation of alkynes has been explored and achieved using 1 mol % organic dye Eosin Y as the photocatalyst and a catalytic amount of thiol as the radical quencher. The corresponding alkenylsilanes were provided with high reg
Evaluation of cyclopentyl methyl ether (CPME) as a solvent for radical reactions
Kobayashi, Shoji,Kuroda, Hiroyuki,Ohtsuka, Yuta,Kashihara, Takashi,Masuyama, Araki,Watanabe, Kiyoshi
, p. 2251 - 2259 (2013/03/29)
We have explored the potential of cyclopentyl methyl ether (CPME) as a solvent for radical reactions. Hydrostannation, hydrosilylation, hydrothiolation, and tributyltin hydride mediated reductions were successfully carried out in CPME. GC-MS analysis indicated that CPME degraded into methyl pentanoate, cyclopentanone, 2-cyclopenten-1-ol, and cyclopentanol under thermal radical conditions, albeit only slightly. We also achieved radical-containing one-pot reactions in CPME as a demonstration of its applicability to multi-step reactions.
Safe, facile radical-based reduction and hydrosilylation reactions in a microreactor using tris(trimethylsilyl)silane
Odedra, Arjan,Geyer, Karolin,Gustafsson, Tomas,Gilmour, Ryan,Seeberger, Peter H.
scheme or table, p. 3025 - 3027 (2009/02/04)
A highly efficient system for tris(trimethylsilyl)silane (TTMSS) mediated deoxygenation, dehalogenation and hydrosilylation reactions is described in a microstructured device; this convenient platform enables the scale up of radical-based processes. The Royal Society of Chemistry.
Air-initiated hydrosilylation of unactivated alkynes and alkenes and dehalogenation of halohydrocarbons by tris(trimethylsilyl)silane under solvent-free conditions
Wang, Jialiang,Zhu, Zhenyu,Huang, Wen,Deng, Mingli,Zhou, Xigeng
, p. 2188 - 2192 (2008/09/21)
A highly efficient air-initiated hydrosilylation of unactivated alkynes and alkenes and dehalogenation of halohydrocarbons with tris(trimethylsilyl)silane ((TMS)3SiH) as a reducing agent has been established under solvent-free conditions. These observations demonstrate that the potential and versatility of air to function as a competent initiator for Si-H bond activations. It can rival organic initiators and metal catalysts in its efficiency and is a superior initiating system from economic, environmentally sound and practical perspectives.
Radical-mediated silyl- and germyldesulfonylation of vinyl and (α-fluoro)vinyl sulfones: Application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings
Wnuk, Stanislaw F.,Garcia Jr., Pedro I.,Wang, Zhizhong
, p. 2047 - 2049 (2007/10/03)
Equation presented. Radical-mediated silyl- and germyldesulfonylations of various vinyl and (α-fluoro)vinyl sulfones with tris(trimethylsilyl)silane and germanium hydrides provide access to vinyl and (α-fluoro)vinyl silanes and germanes. Upon oxidative treatment with hydrogen peroxide in basic aqueous solution, the vinyl tris(trimethylsilyl)silanes and -germanes undergo Pd-catalyzed cross-couplings with aryl halides.
Geminal Di(hypersilyl) compounds - The synthesis and structure of bis[tris(trimethylsilyl)silyl]methanol
Gross, Thoralf,Kempe, Rhett,Oehme, Hartmut
, p. 1709 - 1714 (2007/10/03)
Tris(trimethylsilyl)silyllithium (1) reacts with methyl formate in diethyl ether (molar ratio 2:1) to give l,2-di(hypersilyl)ethylene 13. The formation of 13 proceeds through the intermediates formyl tris(trimethylsilyl)silane (4) and lithium bis[tris(trimethylsilyl)silyl]methoxide (5). In diethyl ether, the alkoxide 5 spontaneously eliminates lithium trimethylsilanolate thereby generating l,l-bis(trimethylsilyl)-2-[tris{trimethylsilyl)silyl]silene (9), which undergoes a formal [2+2] cycloaddition with the carbonyl compound 4 to afford 13. This was verified by crossover experiments. In pentane, the alkoxide 5 is moderately stable. Thus, the intermediate 5, prepared by reaction of 1 with tert-butyl formate in pentane, was protonated with water to give the di(hypersilyl)methanol 6 in good yield. The structure of 6 was elucidated by an X-ray crystal structure analysis, which expectedly revealed tremendous distortions of the molecular skeleton. Thus, the spatial demand of the two extended hemispherical (Me3Si)3Si groups forces a widening of the Si-C-Si angle at the central sp3 carbon atom to a value of 135.5°. WILEY-VCH Verlag GmbH, 1997.
Triethylborane Induced Stereoselective Radical Addition of R3SiH to Acetylenes and Stereoselective Reduction of Alkenyl Iodides with Tris(trimethylsilyl)silane
Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2356 - 2364 (2007/10/02)
Triethylborane induced radical addition of various organosilanes (R3SiH) to acetylenes has been studied.Among them, tris(trimethylsilyl)silane (TTMSS) proved to be the best reagent for the hydrosilylation of acetylenic compounds in terms of yield and ster
