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Cuprous iodide is one of the most generally used cuprous salts in labs
Cuprous iodide (CuI), white cubic crystal or beige powder, poisonous.
Steady to light as well as air. Cuprous iodide is nearly insoluble in water and also ethanol, however soluble in liquid ammonia, thin down hydrochloric acid, potassium iodide, potassium cyanide or salt thiosulfate solution, and also can be decayed by focused sulfuric acid as well as focused nitric acid.
It can also remain to collaborate with iodide ions to produce straight [CuI2] -ions, which can be liquified in potassium iodide or sodium iodide remedy.
It reacts with sodium hydroxide to create cuprous oxide, salt iodide as well as water.
Along with basic usages such as reagents, cuprous iodide likewise has several uses in various other areas such as medicine.
Introduction of actual application:
In the presence of 1,2- or 1,3-diamine ligands, cuprous iodide can convert brominated aromatic hydrocarbons, brominated heterocyclic materials and the same plastic bromide into matching iodides.
The reaction is usually carried out in a dioxane solvent, and sodium iodide is used as the iodination reagent.
Aromatic iodides are generally more vigorous than matched chlorides and iodides.
The coupling reaction of 2-bromo-1-octene-3-ol and 1-nonyne in the presence of dichlorobis(triphenylphosphine)palladium(II), cuprous chloride and diethylamine produces 7-methylene Group-8-hexadec-6-ol.
Note: This application scenario is for reference and understanding only, and the specific application should be based on the actual situation
An important role of cuprous iodide is to catalyze the formation of various CC bonds, including diaryl compounds, aryl alkyne compounds, aryl olefin compounds, enyne compounds, 1,3-diene compounds, and 1,3-diene compounds. n-Diacetylene compounds and so on.
For example, under the catalysis of cuprous iodide, benzothiazole and 2-bromopyridine can directly undergo dehydrobromination coupling to obtain 2-position heteroaryl substituted benzothiazole.
Cuprous iodide is also used to catalyze the cyanation reaction and the cross-coupling reaction of aryl halides and electron withdrawing groups a-C.
For example: using Cs2CO3 as an alkaline reagent, cuI can catalyze the coupling reaction of diethyl malonate and iodobenzene. Phenyl-substituted diethyl malonate.
The CN bond forming it can efficiently catalyze the coupling reaction of the CN bond, and can catalyze aryl halides, alkenyl halides and alkynyl halides with aromatic amines, aliphatic amines, amides, imides, azoles, etc. Coupling of compounds.
For example, under the catalysis of Cu1/DMEDA system, a-hydroxypropionamide is coupled with iodobenzene to obtain N-phenyl-a-hydroxypropionamide.
Under this condition, the hydroxyl group in the molecule does not undergo a coupling reaction.
The Ullmann reaction involving C-O bond formation and copper participation is a common method for the synthesis of simple diaryl ethers, but the traditional method has many limitations.
For example: using harsh reaction conditions, strong bases and stoichiometric copper.
Through the introduction of new copper sources, new ligands and different alkaline reagents, the Go coupling reaction involving copper has been greatly developed, with milder conditions and a wider range of substrates.
For example, using N,N-dimethylglycine and Cs2CO3 as ligand and base, cuprous iodide can catalyze the coupling reaction of iodobenzene and phenol at 90°C to obtain diphenyl ether.
Cuprous iodide can not only catalyze the coupling of aryl halides and phenols, but also catalyze the C-O cross-coupling of alkenyl halides and phenols, aryl halides and alcohols and other different types of substrates.
Recently, You et al. directly used hydroxide to react with aryl halides and developed a new method to generate polysubstituted phenols under mild conditions.
C-S bond formation Thioether compounds can also be obtained from a C-S cross-coupling reaction catalyzed by cuprous iodide with halides and corresponding mercaptans.
Under the conditions of copper catalysis, the reactivity of sulfur atoms is generally high, even in the presence of other nucleophiles such as phenols, thioethers can still be formed chemoselectively.
1,3-Dipolar cycloaddition reaction it can be used to catalyze the 1,3-dipolar cycloaddition reaction.
For example, under the catalysis of cuprous iodide, azide compounds can undergo 1,3-dipolar cycloaddition with a variety of alkynes to obtain multi-substituted triazole compounds.
According to related reports: the cycloaddition reaction of alkynyl esters and azomethines catalyzed by cuprous iodide yields two five-membered ring and nitrogen-containing heterocyclic compounds.
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