Protection of hydroxy groups as trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane (HMDS) catalyzed by poly(4-vinylpyridinium tribromide)

2010 ◽  
Vol 75 (5) ◽  
pp. 607-615 ◽  
Author(s):  
Arash Ghorbani-Choghamarani ◽  
Mohammad Ali Zolfigol ◽  
Maryam Hajjami ◽  
Khorshid Darvishi ◽  
Laleh Gholamnia
Keyword(s):  
Room Temperature ◽  
Efficient Procedure ◽  
Mild Conditions ◽  
Trimethylsilyl Ethers ◽  
Hydroxy Groups

A very efficient procedure for the protection of alcohols and phenols is presented. The mixture of 1,1,1,3,3,3-hexamethyldisilazane (HMDS) and catalytic amounts of poly(4-vinylpyridinium tribromide) was found to be effective for the trimethylsilylation of alcohols and phenols. Protection reaction is very simple and performs heterogeneously in acetonitrile at room temperature under mild conditions.

Silica-bonded S-sulfonic acid as a recyclable catalyst for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS)

2010 ◽  
Vol 88 (2) ◽  
pp. 164-171 ◽  
Author(s):  
Khodabakhsh Niknam ◽  
Dariush Saberi ◽  
Hajar Molaee ◽  
Mohammad Ali Zolfigol
Keyword(s):  
Sulfonic Acid ◽  
Room Temperature ◽  
Reaction Times ◽  
Chlorosulfonic Acid ◽  
Hydroxyl Groups ◽  
Secondary Alcohols ◽  
Mild Conditions ◽  
Trimethylsilyl Ethers ◽  
Phenolic Hydroxyl Groups ◽  
Good Range

Silica-bonded S-sulfonic acid (SBSSA) was prepared by the reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in tert-butylmethyl ether, and used as a catalyst for the silylation of hydroxyl groups. A good range of primary, secondary alcohols and phenolic hydroxyl groups were effectively converted into their corresponding trimethylsilyl ethers with hexamethyldisilazane (HMDS) in the presence of catalytic amounts of SBSSA under mild conditions at room temperature with short reaction times and in good-to-excellent yields. An excellent chemoselective silylation of hydroxyl groups in the presence of other functional groups was also observed. The heterogeneous catalyst was recycled for 30 runs upon the reaction of benzyl alcohol with HMDS without lossing its catalytic activity.

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

scholarly journals Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1897
Author(s):  
Hideyasu China ◽  
Nami Kageyama ◽  
Hotaka Yatabe ◽  
Naoko Takenaga ◽  
Toshifumi Dohi
Keyword(s):  
Aqueous Solution ◽  
Room Temperature ◽  
Practical Method ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Sequential Procedures ◽  
Iodine Compounds ◽  
Practical Synthesis ◽  
Iodosobenzoic Acid ◽  
Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem

Synthesis ◽  
2020 ◽  
Author(s):  
Narendra R. Chaubey ◽  
Anant R. Kapdi ◽  
Biswanath Maity
Keyword(s):  
Total Synthesis ◽  
Room Temperature ◽  
Drug Molecule ◽  
Bond Functionalization ◽  
First Report ◽  
Mild Conditions ◽  
The Past ◽  
Hypnotic Drug ◽  
Free Environment

AbstractOrganophotocatalytic C–H bond functionalization has attracted a lot of attention in the past several years due to the possibility of catalyzing reactions in a metal- and peroxide-free environment. Continuing on these lines, an organophotoredox-catalyzed C–H functionalization of imidazo[1,2-a]pyridines and related heterocycles with bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative­-hypnotic drug molecule.

scholarly journals Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

Elektrostatische Aktivierung der SNAr-Reaktivität durch Sulfonyloniosubstituenten/Electrostatic Activation of SNAr-Reactivity by Sulfonylonio Substituents

2001 ◽  
Vol 56 (12) ◽  
pp. 1360-1368 ◽  
Author(s):  
Robert Weiss ◽  
Frank Pühlhofer
Keyword(s):  
Room Temperature ◽  
Reaction Path ◽  
Mild Conditions ◽  
Electrostatic Effect

Abstract 4-Fluorobenzenesulfonyl chloride (1) and pentafluorobenzenesulfonyl chloride (2) are transformed into the corresponding N-sulfonylpyridinium triflates 4a-d by treatment with one equivalent of the reagent pair L/TMSOTf (L = 4-dimethylaminopyridine (DMAP), 4-ferf-butylpyridine (TBUPY), 1-methylimidazole (NMI); TMSOTf = trimethylsilyl triflate). Due to the electrostatic effect of the sulfonylonio function, SNAr reactions on these systems can be performed under mild conditions. So the reaction of 2 with excess DMAP/TMSOTf leads by way of peronio substitution to hexakis[(4-dimethylamino)-l-pyridinio]benzene hexa-kis(trifluoromethansulfonate) (7) [22] at room temperature. Additionally, a new reaction path to 4-(1-pyridinio)-substituted benzenesulfonamides, a class of pharmaceutically interesting substances, is shown.

Facile synthesis of 5-hydroxymethylfurfural: a sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins

RSC Advances ◽  
2015 ◽  
Vol 5 (121) ◽  
pp. 100401-100407 ◽  
Author(s):  
Rajamani Rajmohan ◽  
Subramaniyan Gayathri ◽  
Pothiappan Vairaprakash
Keyword(s):  
Room Temperature ◽  
Solid Support ◽  
Raw Material ◽  
Facile Synthesis ◽  
Mild Conditions

In a simple and conceptually designed method for the dehydration of fructose on a solid support, 5-hydroxymethylfurfural (HMF) was synthesized in more than 95% isolated yield from fructose under very mild conditions at room temperature.

scholarly journals New methylphenylsiloxane resin based on alkoxysilanes

2019 ◽  
Vol 59 (7) ◽  
pp. 142-149
Author(s):  
Andrey M. Kontorov ◽  
Keyword(s):  
Kinematic Viscosity ◽  
Room Temperature ◽  
Raw Materials ◽  
Argon Atmosphere ◽  
29Si Nmr ◽  
Synthesis Conditions ◽  
Residual Functional ◽  
29Si Nmr Spectra ◽  
Hydroxy Groups

Currently interested in the reaction for producing oligosilsesquioxanes based on acidolysis alkoxysilanes. In this regard, the author was given the following tasks: development of optimal synthesis conditions; preparation of new methylphenylsiloxane resins with different properties. In this paper, the properties of new methylphenylsiloxane resins (MPR) with various radicals in silicon were studied. New IFSS were obtained by a new universal technology-acidolysis of a mixture of methyltriethoxysilane (MTEOS) and phenyltriethoxysilane (PTEOS) with various radicals, which are environmentally friendly raw materials. The obtained MPR were characterized by NMR spectroscopy on 1H and 29Si nuclei. Spectra were recorded at room temperature in deuteroacetone using Bruker AM-360 Fourier spectrometer. 29Si NMR spectra were measured using the pulse program "Inverse Gated Heteronuclear Decoupling". The content of residual functional groups (Si-OH, Si-OEt) in IFSS was determined by functional analysis methods. Determination of ethoxy groups and hydroxy groups was carried out by iodometric and aluminohydride method, respectively. Thermogravimetric analysis was performed on the device Derivatograph-H (firm Mom). TGA studies were carried out in the argon atmosphere and in the air at a heating rate of 10 ºC/min. Measurements of kinematic viscosity of 20 % and 50% by weight. toluene solutions of MPR were carried out at 20 °C on the viscometer HPV-2. The reaction acidolysis of methyltriethoxysilane and oligophenylenes is a convenient and versatile method for the synthesis of new heat-resistant resins methylphenylsiloxanes. In the course of the study, it was found that the resins obtained on the basis of organoalkoxysilanes are characterized by higher thermal and thermo-oxidative stability.

scholarly journals H/D Exchange Under Mild Conditions in Arenes and Unactivated Alkanes with C6D6 and D2O Using Rigid, Electron-rich Iridium PCP Pincer Complexes

2020 ◽  
Author(s):  
Joel D. Smith ◽  
George Durrant ◽  
Daniel Ess ◽  
Warren Piers
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Room Temperature ◽  
Pincer Complexes ◽  
Synthesis And Characterization ◽  
Hydrogen Isotope Exchange ◽  
Mild Conditions ◽  
Highly Active ◽  
Pcp Pincer

<div>The synthesis and characterization of an iridium polyhydride complex (Ir-H4)</div><div>supported by an electron-rich PCP framework is described. This complex readily loses molecular</div><div>hydrogen allowing for rapid room temperature hydrogen isotope exchange (HIE) at the hydridic</div><div>positions and the α-C-H site of the ligand with deuterated solvents such as benzene-d6, toluene-d8</div><div>and THF-d8. The removal of 1-2 equivalents of molecular H2 forms unsaturated iridium carbene</div><div>trihydride (Ir-H3) or monohydride (Ir-H) compounds that are able to create further unsaturation</div><div>by reversibly transferring a hydride to the ligand carbene carbon. These species are highly active</div><div>hydrogen isotope exchange (HIE) catalysts using C6D6 or D2O as deuterium sources for the</div><div>deuteration of a variety of substrates. By modifying conditions to influence the Ir-Hn speciation,</div><div>deuteration levels can range from near exhaustive to selective only for sterically accessible sites.</div><div>Preparative level deuterations of select substrates were performed allowing for procurement of</div><div>>95% deuterated compounds in excellent isolated yields; the catalyst can be regenerated by</div><div>treatment of residues with H2 and is still active for further reactions.</div>

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