Bis(4-tert-butylphenyl)iodonium P-toluenesulfonate

"Bis (4-tert-butylphenyl) iodonium p-toluenesulfonate" is an important reagent in the field of organic synthesis. Its main application range involves a wide range of organic reaction processes.
In the field of arylation reactions, this reagent is a key. Due to its unique structural properties, it can effectively transfer the aryl moiety to a specific substrate. For example, when reacting with substrates containing active hydrogen, aryl groups can be skillfully introduced to construct novel carbon-carbon or carbon-heteroatomic bonds. This is of great significance in the field of pharmaceutical chemistry. The synthesis of many drug molecules relies on this reaction to introduce key aryl structure fragments and enhance the activity and specificity of drugs.
Furthermore, in the reaction system initiated by free radicals, bis (4-tert-butylphenyl) iodonium p-toluenesulfonate also exhibited excellent efficacy. It can generate iodine radicals under specific conditions, which in turn triggers a series of free radical chain reactions. Radical addition reactions such as olefins, with the participation of this reagent, precise addition path control can be achieved to synthesize olefins with diverse structures, which provides an effective way for the preparation of polymer materials with special properties in the field of materials science.
In addition, in some photocatalytic reactions, this reagent can act as a co-catalyst of photosensitizer to synergistically enhance the efficiency of photocatalytic systems. It can promote the separation and transmission of photogenerated carriers through its own electron transfer process, thereby accelerating the rate of photocatalytic reaction, enabling the reaction to proceed efficiently under milder conditions, demonstrating a unique advantage in green chemical synthesis.

The author of "Tiangong Kaiwu" is also an ancient scientific and technological book. In ancient Chinese, it describes the chemical properties of "Bis (4-tert-butylphenyl) iodonium P-toluenesulfonate".
This compound has unique chemical properties. It is an organic iodized salt. In the field of organic synthesis, it is often used as an iodizing reagent and an oxidizing reagent because of its active chemical activity of iodine atoms.
In the electrophilic substitution reaction, iodine positive ions can be released, which can make aromatic hydrocarbons and other substrates undergo iodization reactions and introduce iodine atoms at specific locations. It has high reactivity, can react with a variety of electron-rich organic compounds, and has good selectivity. It can be directed to substituted products at specific positions according to the structure and reaction conditions of the substrate.
And because of its oxidizing ability, it can oxidize some functional groups. If alcohol compounds are oxidized to aldodes or ketones, this oxidation process is often carried out under mild reaction conditions, which is very helpful for the construction of complex molecular structures in organic synthesis.
And the stability of the compound is also considerable. Under normal storage conditions, it can maintain the stability of its chemical structure. However, when it encounters specific chemicals such as strong reducing agents, strong acids or strong bases, its structure and properties will also change, participating in various chemical reactions and exhibiting rich chemical behaviors. This is also an important chemical property of "Bis (4 - tert - butylphenyl) iodonium P - toluenesulfonate".

The method for preparing bis (4-tert-butylphenyl) iodonium p-toluenesulfonate is as follows:
First take an appropriate amount of 4-tert-butyliodobenzene, place it in a clean reaction bottle, add an appropriate amount of anhydrous dichloromethane as a solvent, and stir to fully dissolve it. In this solution, slowly add metered silver trifluoromethanesulfonate. This process needs to be carried out at low temperature and protected from light, usually at about 0 ° C. Silver trifluoromethanesulfonate reacts with 4-tert-butyliodobenzene to form 4-tert-butylphenyl trifluoromethanesulfonate iodonium intermediate. During the reaction, close attention should be paid to the color change and precipitation formation of the reaction system.
After the reaction is completed, the reaction mixture is filtered through a filter paper to remove the resulting silver halide precipitate. After that, the filtrate is transferred to another reaction flask, and an appropriate amount of sodium p-toluenesulfonate is added. In this step, the sodium p-toluenesulfonate anion undergoes an anion exchange reaction with the 4-tert-butylphenyltrifluoromethanesulfonate iodonium intermediate to generate bis (4-tert-butylphenyl) iodonium p-toluenesulfonate.
After the reaction is completed, the mixture is left to stand and stratified, the organic phase is taken, dried with anhydrous sodium sulfate, and the residual moisture is removed. After that, the solvent dichloromethane is evaporated under reduced pressure with a rotary evaporator In order to obtain pure bis (4-tert-butylphenyl) iodonium p-toluenesulfonate, the crude product can be recrystallized with a suitable organic solvent, such as ethyl acetate-n-hexane mixed solvent. After cooling, crystallization, suction filtration, drying and other steps, the final high-purity bis (4-tert-butylphenyl) iodonium p-toluenesulfonate product can be obtained. The whole process requires strict control of the reaction conditions and the amount of each reagent to ensure the yield and purity of the product.

Bis (4-tert-butylphenyl) iodonium p-toluenesulfonate is a commonly used reagent in organic synthesis. When storing and transporting, many matters must be paid attention to.
First words storage. This reagent is quite sensitive to light and heat, and should be placed in a cool, dry and dark place. Light and high temperature can easily cause it to decompose and deteriorate, and damage its chemical activity. The temperature should be controlled between 15 ° C and 25 ° C, and the humidity should be 40% - 60%. It should also be kept away from fire sources and oxidants. Because of its certain chemical activity, strong oxidants or fire sources may react violently and endanger safety. At the same time, it must be sealed and stored to prevent moisture intrusion. Moisture can hydrolyze the reagent, changing its chemical structure and affecting the use effect.
As for transportation, there are also strict requirements. This reagent is classified as a chemical, and relevant regulations and standards must be followed during transportation. The packaging must be strong and well sealed to prevent leakage. During transportation, avoid violent vibration and collision to prevent package damage. In summer transportation, special attention should be paid to cooling to prevent high temperature from causing it to decompose. Transportation vehicles should be equipped with corresponding fire protection and leakage emergency treatment equipment, just in case. Transportation personnel also need to be professionally trained and familiar with the characteristics of reagents and emergency treatment methods.
This is to ensure the stability and safety of Bis (4-tert-butylphenyl) iodonium p-toluene sulfonate during storage and transportation, so as to prepare for organic synthesis experiments.

Bis (4-tert-butylphenyl) iodonium P-toluenesulfonate is a commonly used organic compound, which has a wide range of uses in the field of organic synthesis. It can react with many compounds, for example:
First, nucleophilic substitution reaction. Due to the high activity of iodine ions in this compound, it is vulnerable to attack by nucleophiles. If it encounters a carbon-containing nucleophilic reagent, such as enol salts, the carbon anion site of the nucleophilic reagent will attack the iodine ion, causing the breaking of the carbon-iodine bond and forming a new carbon-carbon bond, which is crucial for the construction of the carbon skeleton of complex organic molecules.
Its oxidation reaction. The compound can exhibit certain oxidizing properties and can oxidize some reducing functional groups. If reacted with sulfur-containing compounds, the oxidation state of sulfur atoms can be increased, the oxidative transformation of sulfur compounds can be realized, and sulfur-containing products with different oxidation states can be obtained.
Third, radical reaction. Under specific conditions, Bis (4-tert-butylphenyl) iodonium P-toluenesulfonate can initiate free radical reactions. When illuminated or a suitable initiator is added, iodine ions can produce free radical intermediates, which can react rapidly with unsaturated compounds such as olefins, and generate various addition products through mechanisms such as free radical addition, providing a novel path for organic synthesis.
Fourth, arylation reaction. It can be used as an arylation reagent to introduce aryl groups into other molecules. When reacted with compounds containing active hydrogen, such as phenols and amines, aryl groups can be substituted for active hydrogen, thereby preparing arylated products with special structures and functions, which is of great significance in the fields of medicinal chemistry and materials science.