33035-41-5

Usage

Uses

Used in Organic Synthesis:
Iodomesitylene diacetate is utilized as a reagent for aromatic iodination reactions, which is crucial for the synthesis of various organic compounds. Its selective iodination ability allows for the efficient and precise incorporation of iodine into aromatic systems, facilitating the creation of a broad spectrum of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Iodomesitylene diacetate serves as a key precursor for the preparation of iodinated compounds. These iodinated compounds are often essential in the development of drugs with specific therapeutic properties, such as contrast agents for imaging studies or compounds with antimicrobial or antiviral activities.
Used in Chemical Research:
Iodomesitylene diacetate is also employed in chemical research as a tool to study the reactivity and properties of aromatic systems. Its selective iodination capability provides researchers with a means to investigate the effects of iodine substitution on molecular structures and their subsequent chemical behavior.
Used in Material Science:
In the field of material science, Iodomesitylene diacetate contributes to the development of new materials with unique properties. The iodination of aromatic systems can lead to materials with enhanced electrical, optical, or magnetic characteristics, which can be applied in various high-tech applications, such as organic electronics or advanced sensors.

Upstream product

• 79-21-0 peracetic acid 
• 4028-63-1 iodomesitylene 
• 64-19-7 acetic acid 
• 56021-54-6 iodine triacetate 
• 108-67-8 1,3,5-trimethyl-benzene 
• 108-24-7 acetic anhydride 
• 2100-22-3 1-iodo-2,4,6-triisopropylbenzene 
• 717-74-8 1,3,5-triisopropyl benzene 

Downstream Products

• 37985-29-8 1-(2,4,6-trimethylphenyl)-2-propyne 
• 131251-59-7 1-(2,4,6-trimethyl-3-iodophenyl)-1,2-propadiene 
• 131251-57-5 1-(2,4,6-trimethyl-3-iodophenyl)-2-propyne 
• 139139-80-3 bis(2,4,6-trimethylphenyl)iodonium triflate 
• 1039396-34-3 (E)-3-(mesityl(phenyl)methylene)-1-methylindolin-2-one 
• 1176325-58-8 C₁₇H₁₄F₆INO₂S 
• 1380240-10-7 mesityl(2-methylprop-1-en-1-yl)iodonium trifluoromethanesulfonate 

Relevant academic research and scientific papers

Decarboxylative C-H alkylation of heteroarene N-oxides by visible light/copper catalysis

This paper reports a highly site-selective alkylation of heteroarene N-oxides using hypervalent iodine(III) carboxylates to serve as an alkylating agent in the presence of a cheap copper catalyst under visible light conditions. This mild method proceeds at room temperature in an air atmosphere and can withstand various heteroarene N-oxides as well as various primary, secondary, and tertiary alkyl carboxylic acids. It also provides a practical method for enabling the rapid conversion of commercially available raw materials into medically relevant “drug-like” molecules.

Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds

Non-iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one-pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.

Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.

N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Synthesis of O -Aroyl- N, N -dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N, N -Dimethylformamide

An efficient protocol for the synthesis of O -aroyl- N, N -dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N, N -dimethylformamide is mediated by hypervalent iodine and

NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles

The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.

Room-Temperature Gold-Catalysed Arylation of Heteroarenes: Complementarity to Palladium Catalysis

Tailoring of the pre-catalyst, the oxidant and the arylsilane enables the first room-temperature, gold-catalysed, innate C?H arylation of heteroarenes. Regioselectivity is consistently high and, in some cases, distinct from that reported with palladium ca

Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives

A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments. Polyols: The reported copper-catalyzed oxy-alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn-1,3-carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.

Synthesis and reactivity of aryl(alkynyl)iodonium salts

The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.