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
• Article Data: 9

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

General Description

Phenyl(trimethylsilylethynyl)iodonium triflate is a chemical compound used in organic synthesis as a powerful and selective source of phenyl cations. It is a versatile reagent in various transformations, including nucleophilic substitutions, cycloadditions, and C-H activation reactions. The triflate counterion enhances the reactivity of the cationic species, making it a valuable tool in synthetic chemistry. phenyl(trimethylsilylethynyl)iodonium triflate is stable and can be easily handled in the laboratory, making it a popular choice for researchers working in the field of organic chemistry. Overall, phenyl(trimethylsilylethynyl)iodonium triflate is a valuable and effective reagent for carrying out a wide range of organic reactions.

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

• 142144-85-2 (3-methoxycarbonyl-5-trimethylsilyl-4-pyrazolyl)-phenyliodonium trifluoromethanesulfonate 
• 142144-87-4 (3-ethoxycarbonyl-5-trimethylsilyl-4-pyrazolyl)-phenyliodonium trifluoromethanesulfonate 
• 142363-49-3 [(Trimethylsilyl)ethynyl](triphenyl)phosphonium triflate 
• 33567-66-7 N,N-Diphenyl<(trimethylsilyl)ethinyl>amin 
• 123775-84-8 trimethyl((phenylselanyl)ethynyl)-silane 
• 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 
• 205885-33-2 N-(but-3-en-1-yl)-4-methyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide 
• 205885-35-4 4-methyl-N-(1-phenylbut-3-enyl)-N-(trimethylsilylethynyl)benzenesulfonamide 
• 205885-37-6 N-(1-Allyl-but-3-enyl)-4-methyl-N-trimethylsilanylethynyl-benzenesulfonamide 
• 205885-36-5 N-(1-Allyl-pentyl)-4-methyl-N-trimethylsilanylethynyl-benzenesulfonamide 
• 205885-34-3 4-Methyl-N-(2-phenyl-but-3-enyl)-N-trimethylsilanylethynyl-benzenesulfonamide 
• 247155-40-4 N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine 

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

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.

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.