91523-99-8Relevant academic research and scientific papers
Introduction of PEG-SANM nanocomposite as a new and highly efficient reagent for the promotion of the silylation of alcohols and phenols and deprotection of the silyl ethers
Shirini, Farhad,Shojaei, Abdollah Fallah,Heirati, Seyedeh Zahra Dalil
, p. 944 - 951 (2016)
Poly (ethylene glycol)-sulfonated sodium montmorillonite (PEG-SANM) nanocomposite was prepared by a simple method and characterized using XRD, TGA, SEM, TEM, and FT-IR techniques. After preparation and characterization, this reagent was used as a highly efficient and reusable solid acid catalyst for the chemoselective silylation of alcohols and phenols and deprotection of the obtained silyl ethers. Themethod offers several advantages including high to excellent yields of the products, short reaction times, easy preparation of the catalyst and easy work-up procedure. In addition, the catalyst can be recycled and reused at least for five times without significant decrease in the catalytic activity.
Iron-Catalyzed Silylation of Alcohols by Transfer Hydrosilylation with Silyl Formates
Godou, Timothé,Chauvier, Clément,Thuéry, Pierre,Cantat, Thibault
supporting information, p. 2473 - 2477 (2017/10/26)
An iron catalyst is shown for the first time to promote transfer hydrosilylation with silyl formates and is utilized for the silylation of alcohols. Attractive features of this protocol include the use of an earth-abundant transition-metal catalyst, mild reaction conditions, and the release of gases as the only byproducts (H 2 and CO 2).
P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
Shirini, Farhad,Fallah-Shojaei, Abdollah,Abedini, Masoumeh,Samavi, Laleh
, p. 1699 - 1712 (2016/07/27)
P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.
First example of borirane synthesis by α-olefins reaction with BCl3·SMe2 Catalyzed with (η5-C5H5)2TiCl2
Khusainova,Khafizova,Tyumkina,Dzhemilev
, p. 1517 - 1523 (2015/12/30)
New method was developed of the synthesis of 2-phenyl(alkyl, benzyl, phenoxy)-1-chloroboriranes via reaction of α-olefins with BCl3·SMe2 catalyzed by Cp2TiCl2. The method is based on the boracyclopropanes (boriranes) formation resulting from transmetallation of titanacyclopropanes arising from the reaction of α-olefins with Cp2TiCl2. The calculations were fulfilled of thermodynamic and activation parameters of possible reaction routes.
Poly(4-vinylpyridine) catalyzed chemoselective O-TMS protection of alcohols and phenols and N-Boc protection of amines
Shirini, Farhad,Khaligh, Nader Ghaffari
, p. 495 - 502 (2013/02/22)
Poly(4-vinylpyridine) (PVP) acts as an efficient and reusable catalyst for the selective and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and N-tert-butoxycarbonylation of amines with (Boc)2O. All reactions were performed under mild conditions in good to high yields. Iranian Chemical Society 2012.
Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
Jereb, Marjan
experimental part, p. 3861 - 3867 (2012/06/30)
An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol %) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process.
Gold nanoparticles-catalyzed activation of 1,2-disilanes: Hydrolysis, silyl protection of alcohols and reduction of tert-benzylic alcohols
Gryparis, Charis,Stratakis, Manolis
supporting information, p. 10751 - 10753,3 (2020/09/02)
Gold nanoparticles supported on TiO2 catalyze under mild conditions the activation of a series of 1,2-disilanes towards hydrolysis and alcoholysis, with concomitant evolution of H2 gas. For the case of tert-benzyl alcohols, the main or only pathway is reduction to the corresponding alkanes.
Succinimide-N-sulfonic acid: A mild, efficient, and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols
Shirini,Khaligh, Nader Ghaffari
experimental part, p. 2156 - 2165 (2012/04/10)
Succinimide-N-sulfonic acid (SuSA) is easily prepared by the reaction of succinimide with chlorosulfonic acid. This reagent is able to efficiently catalyze the chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). All reactions were performed under mild reaction conditions, giving excellent yields. Copyright Taylor & Francis Group, LLC.
DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride
Poisson, Thomas,Dalla, Vincent,Papamica?l, Cyril,Dupas, Georges,Marsais, Francis,Levacher, Vincent
, p. 381 - 386 (2008/01/08)
A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.
Efficient o-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions
Amantini,Fringuelli,Pizzo,Vaccaro
, p. 6734 - 6737 (2007/10/03)
A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 °C. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.
