133816-00-9

Basic information

• Product Name: phenyl(trimethylsilylethynyl)iodonium triflate
• Synonyms: phenyl(trimethylsilylethynyl)iodonium triflate
• CAS NO: 133816-00-9
• Molecular Weight: 450.293
• Mol File: 133816-00-9.mol

Chemical Properties

• CAS DataBase Reference: phenyl(trimethylsilylethynyl)iodonium triflate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl(trimethylsilylethynyl)iodonium triflate(133816-00-9)
• EPA Substance Registry System: phenyl(trimethylsilylethynyl)iodonium triflate(133816-00-9)

Safety Data

• Hazardous Substances Data: 133816-00-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenyl(trimethylsilylethynyl)iodonium triflate is employed as a reagent for generating phenyl cations, which are crucial intermediates in a multitude of organic reactions. Its application is instrumental in facilitating nucleophilic substitutions, cycloadditions, and C-H activation reactions, thereby broadening the scope of synthetic pathways available to chemists.
Used in Research Laboratories:
In research settings, phenyl(trimethylsilylethynyl)iodonium triflate is used as a reliable and stable reagent for conducting complex organic reactions. Its ease of handling and stability make it a preferred choice for researchers working on innovative synthetic methodologies and exploring novel chemical transformations.
Used in Pharmaceutical Industry:
Phenyl(trimethylsilylethynyl)iodonium triflate is utilized as a key reagent in the synthesis of pharmaceutical compounds, particularly in the development of new drugs and drug candidates. Its ability to generate phenyl cations and participate in various organic reactions aids in the creation of diverse molecular structures with potential therapeutic applications.
Used in Material Science:
In the field of material science, phenyl(trimethylsilylethynyl)iodonium triflate is applied as a reagent for the synthesis of novel materials with unique properties. Its role in organic reactions contributes to the development of advanced materials for various applications, including electronics, energy storage, and nanotechnology.
Overall, phenyl(trimethylsilylethynyl)iodonium triflate is a multifaceted reagent with applications spanning across various industries, including organic synthesis, research, pharmaceuticals, and material science, due to its ability to generate phenyl cations and participate in a wide range of chemical transformations.

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 142144-87-4 (3-ethoxycarbonyl-5-trimethylsilyl-4-pyrazolyl)-phenyliodonium trifluoromethanesulfonate 
• 33567-66-7 N,N-Diphenyl<(trimethylsilyl)ethinyl>amin 
• 205885-30-9 N-Benzyl-C,C,C-trifluoro-N-trimethylsilanylethynyl-methanesulfonamide 
• 205885-32-1 N-benzyl-N-(trimethylsilanylethynyl)benzamide 
• 205885-29-6 N-benzyl-N-trimethylsilanylethynyl-4-methylbenzenesulphonamide 
• 247155-40-4 N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine 
• 247155-31-3 4-methyl-N-(4-trimethylsilanyl-but-3-ynyl)-N-trimethylsilanylethynyl-benzenesulfonamide 
• 247155-36-8 4-methyl-N-(4-phenyl-but-3-ynyl)-N-trimethylsilanylethynyl-benzenesulfonamide 
• 247155-32-4 N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-3-ynyl]-4-methyl-N-trimethylsilanylethynyl-benzenesulfonamide 
• 247155-35-7 C₂₅H₃₂N₂O₄S₂Si 
• 309947-69-1 4-methyl-N-trimethylsilanylethynyl-N-(5-trimethylsilanyl-pent-4-ynyl)-benzenesulfonamide 
• 309947-70-4 4-methyl-N-trimethylsilanylethynyl-N-(6-trimethylsilanyl-hex-5-ynyl)-benzenesulfonamide 
• 22409-58-1 (p-nitrophenoxy)acetylene 

Relevant articles and documents

An alternative synthesis of alkynyl(phenyl)iodonium triflates using (diacetoxyiodo)benzene and alkynylsilanes

Phenyl(trimethylsilylethynyl)iodonium triflate (1a) was prepared in high yields (76-88%) by using the PhI(OAc)2/TfOH or PhI(OAc)2/Tf2O reagent systems. This procedure was also applied to the preparation of other alkynyliod

Straightforward Synthesis of a Vicinal Double-Bridgehead Iodo Trimethylsilyl Octacycle: Unprecedented Lack of Reactivity of the Silyl Group in the Presence of Fluoride Anions

A convenient synthesis of an octacyclic compound containing an iodo and a trimethylsilyl group in vicinal double-bridgehead positions, as a possible precursor of a pyramidalized alkene, is described. The key step of the synthesis consists of a double nucl

Ethynylbenziodoxolones (EBX) as reagents for the ethynylation of stabilized enolates

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scannin

Organocatalytic alkynylation of densely functionalized monofluorinated derivatives: C(sp3)-C(sp) coupling

Organocatalytic alkynylation of nucleophilic fluorocarbons using hypervalent iodine compounds under cinchona-based catalysis, namely using O-allyl N-anthracenyl cinchona alkaloid derivative II, is described. The reaction gives the final fluoro-propargyl compounds in good to excellent yields (up to 91%) and with moderate to low enantioselectivity (up to 61% ee). The reaction represents the first example of the use of hypervalent iodine compounds for the construction of fluorinated compounds and opens access to the preparation of biologically attractive compounds such as 1,2,3-triazoles.

Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine

(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.

Direct alkynylation of thiophenes: Cooperative activation of TIPS-EBX with gold and Bronsted acids

United we stand! Cooperative activation of the hypervalent-iodine reagent TIPS-EBX with a gold catalyst and a Bronsted acid allowed the first direct ethynylation of thiophenes at room temperature (see scheme; TFA = trifluoroacetic acid). The obtained ethynylthiophenes are important building blocks for organic dyes and electronic materials.

Direct alkynylation of indole and pyrrole heterocycles

Chemical Equitation Presentation Easy does it: The unique properties of benziodoxolone alkynyl periodinane l and gold catalysts have allowed the development of a high yielding, operationally simple (room temperature, no dry sol-vents or inert conditions, commercially available catalyst) reaction for the introduction of silylacetylenes on a large range of indole and pyrrole heterocycles with a wide range of functional groups (see scheme).

Preparation of enantioenriched axially chiral anilides via [2+2+2] cycloaddition of 1,6-diynes with trimethylsilylynamides

The rhodium-catalyzed enantioselective [2+2+2] cycloaddition of 1,6-diynes with teimethylsilylynamides provides enantioenriched axially chiral anilides in poor to good yields with good to excellent enantioselectivity. Trimethylsilylynamides can be readily