Synonyms:TMSCN;trimethylsilyl cyanide
99% *data from raw suppliers
Trimethylsilyl cyanide, 97% *data from reagent suppliers
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There total 54 articles about Trimethylsilyl cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 96.0%
Reference yield: 93.0%
Reference yield: 88.0%
The study presents a catalytic 1,2-dicyanation of alkynes using palladium(II) catalysis under aerobic conditions. The reaction involves the use of trimethylsilyl cyanide (TMSCN) and various alkynes, including both aromatic and aliphatic substrates, to achieve high syn-selectivity in the formation of 1,2-dicyano adducts. The purpose of the chemicals used in the study is to investigate the stereoselective cyanation pathways, which include syn- and anti-cyanopalladation to alkynes activated by Pd(II). The study also explores the influence of substrate structure on stereoselectivity and the role of molecular oxygen in the catalytic cyanation process.
The research aimed to develop an enantioselective cyanation process for the synthesis of chiral β-nitronitriles, which are valuable intermediates for the preparation of unnatural chiral β-amino acids. The study utilized a salen–titanium complex as a catalyst to achieve this via the silyl nitronate intermediate, resulting in high yields (up to 90%) and enantioselectivity ratios (up to 92:8). The catalyst demonstrated a high turnover frequency even at room temperature and was effective on a 10 mmol scale with only a slight decrease in enantioselectivity. The process was found to be unique as it did not require protonic additives, which are typically necessary for the in situ formation of HCN and maintaining high turnovers in conjugate cyanation catalysts. The study confirmed the silyl nitronate intermediate pathway through in situ 1H NMR investigation, providing a new approach to the synthesis of β-amino acids. Key chemicals used in the process included various nitroolefins, TMSCN (trimethylsilyl cyanide), and the salen–titanium catalyst.
This research presents a novel three-component strategy for the cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes using a copper catalyst. The purpose of the study is to develop a rapid and concise method for the synthesis of addition-carbocyclization products, which are valuable building blocks in the discovery of lead compounds and biologically active CF3-containing heterocycles. The reaction proceeds smoothly under moderate temperatures, tolerating a broad substrate scope, and providing a new protocol for the synthesis of CF3-containing nitriles and azides. Key chemicals used in the process include 1,6-enynes, Togni's reagent, trimethylsilyl cyanide (TMSCN) or trimethylsilyl azide (TMSN3), and copper catalysts such as Cu(OAc)2 and CuBr, along with ligands like 1,10-phenanthroline. The research concludes that this copper-catalyzed approach is an efficient strategy for 1,6-enyne modification, with potential applications in organic chemistry and biology.
The research presents a study on the synthesis of α-iminonitriles, also known as imidoyl cyanides, which are valuable precursors for a variety of functional groups and nitrogen-containing heterocycles. The researchers developed an oxidative three-component Strecker reaction using a biphasic solvent system (toluene/H2O) with Oxone as the oxidizing agent, tetra-n-butylammonium bromide (TBAB) as a phase-transfer catalyst, and sodium bicarbonate as a buffer. The reaction involves aldehydes, amines, and trimethylsilyl cyanide (TMSCN) and was found to be applicable to a broad range of substrates, including aromatic and aliphatic aldehydes and amines with different electronic and steric properties. The study optimized the reaction conditions, which included the concentration of reactants, the stoichiometry of Oxone and TBAB, and the use of sodium bicarbonate to buffer the reaction mixture. The experiments yielded α-iminonitriles in good to excellent yields and demonstrated high chemoselectivity. The synthesized compounds were characterized using various analytical techniques, including NMR, IR, HRMS, and melting point determination, with the reaction conditions and yields detailed in Tables 1 and 2 of the paper.
The research describes the total synthesis of four marine alkaloids, rhopaladins A-D, isolated from the Okinawan marine tunicate Rhopalaea sp. The synthesis involves two key steps: an imidate-based cyclization with tryptophan esters to form the imidazolinone unit, and a new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes using trimethylsilyl cyanide followed by oxidation with DDQ. The synthesis starts from indol-3-yl-carbonyl nitriles, which are transformed into imidates and then coupled with tryptophan esters. The final O-demethylation step yields rhopaladins A and B. The study also details the preparation of necessary precursors, such as (1H-indol-3-yl)-(trimethylsiloxy)acetonitrile and (5-bromo-1H-indol-3-yl)carbonyl nitrile, using various reagents like TMSCN and DDQ. The synthesized compounds were characterized by spectroscopic data, and the methods developed offer advantages in terms of yield, reaction time, and tolerance towards different substituents.
The study presents a novel method for synthesizing benzyl isocyanides from benzyl halides using silver salts (AgClO4, AgBF4, or AgOTf) and trimethylsilyl cyanide (TMSCN) in CH2Cl2, followed by cleavage of the carbon–silicon bond with aqueous NaHCO3 or TBAF. This method provides a convenient and efficient route to prepare benzyl isocyanides, which are important reactants for various multi-component reactions and have potential applications in complex formation and biological activities. The researchers found that the reaction is versatile and can tolerate a variety of substituents on the benzyl ring, although electron-withdrawing groups may reduce reactivity. The study also elucidates the reaction mechanism, suggesting that an intermediate ionic compound with a TMS group is formed during the process.
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