29540-84-9

Usage

Uses

Used in Organic Synthesis:
4-Chlorophenyl trifluoromethanesulfonate is used as a reagent in organic synthesis for the introduction of the trifluoromethanesulfonyl (Tf) group. Its high reactivity allows it to participate in various reactions, making it a valuable tool for chemists in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-chlorophenyl trifluoromethanesulfonate is used as a key intermediate in the synthesis of various drugs. Its ability to introduce the Tf group can enhance the properties of pharmaceutical compounds, such as solubility, stability, and bioavailability, leading to improved therapeutic effects.
Used in Agrochemical Production:
4-Chlorophenyl trifluoromethanesulfonate is also utilized in the production of agrochemicals, including pesticides and herbicides. The introduction of the Tf group can improve the effectiveness and selectivity of these chemicals, resulting in more efficient and environmentally friendly agricultural products.
Used in Materials Science:
In the field of materials science, 4-chlorophenyl trifluoromethanesulfonate is employed in the development of new materials with unique properties. The incorporation of the Tf group can enhance the performance of materials in various applications, such as in electronics, coatings, and adhesives, by improving their stability, durability, and other characteristics.

InChI:InChI=1/C7H4ClF3O3S/c8-5-1-3-6(4-2-5)14-15(12,13)7(9,10)11/h1-4H

Upstream product

• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 17005-59-3 4-chlorophenoxytrimethylsilane 
• 1493-13-6 trifluorormethanesulfonic acid 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 106-48-9 4-chloro-phenol 
• 109586-39-2 4-iodophenyl trifluoromethanesulfonate 
• 124-63-0 methanesulfonyl chloride 
• 288-32-4 1H-imidazole 
• 29540-81-6 1-(trifluoromethylsulfonyl)-1H-imidazole 
• 1679-18-1 4-Chlorophenylboronic acid 
• 2926-30-9 sodium triflate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 

Downstream Products

• 99-91-2 para-chloroacetophenone 
• 154318-70-4 {2-[1-(4-Chloro-phenyl)-vinyloxy]-ethyl}-dimethyl-amine 
• 74-11-3 para-chlorobenzoic acid 
• 5076-63-1 (4-chlorophenyl)diethyl phosphate 
• 106-48-9 4-chloro-phenol 
• 623-03-0 4-Cyanochlorobenzene 
• 623-26-7 terephthalonitrile 
• 142074-93-9 1-(methoxycarbonyl)-5-(4-chlorophenyl)-3-pyrroline 
• 142074-92-8 (R)-(+)-1-(methoxycarbonyl)-5-(4-chlorophenyl)-2-pyrroline 
• 142074-92-8 (S)-(-)-1-(methoxycarbonyl)-5-(4-chlorophenyl)-2-pyrroline 
• 142074-95-1 1-(ethoxycarbonyl)-5-(4-chlorophenyl)-3-pyrroline 
• 142074-94-0 (R)-(+)-1-(ethoxycarbonyl)-5-(4-chlorophenyl)-2-pyrroline 
• 142074-94-0 (S)-(-)-1-(ethoxycarbonyl)-5-(4-chlorophenyl)-2-pyrroline 
• 142074-97-3 1-(phenoxycarbonyl)-5-(4-chlorophenyl)-3-pyrroline 

Relevant academic research and scientific papers

Palladium-mediated carboxylation of aryl halides (triflates) or benzyl halides using [13C]/[11C]carbon monoxide with tetrabutylammonium hydroxide or trimethylphenylammonium hydroxide

[Carbonyl-11C]carboxylic acids were synthesised using palladium-mediated reaction of [11C]carbon monoxide with aryl halides/triflates and benzyl halides in combination with either tetrabutylammonium hydroxide or trimethylphenylammoni

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage

A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.

Base-promoted selective O-phosphorylation of aryl triflates with P(O)-H compounds

Compared to previous transition metal-catalyzed C-phosphorylation reactions for constructing C–P bonds, in the absence of transition metal catalysts and ligands, a direct O-phosphorylation of aryl triflates selectively occurred with P(O)-H compounds in the presence of a base via the construction of O–P bonds. This transformation proceeds under simple and mild conditions, and provides a new method for the preparation of valuable organophosphoryl compounds from readily available P(O)-H compounds and triflates.

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation

Visible-light-induced decarboxylative sulfonylation of cinnamic acids with aryl sulfonate phenol esters enabled by the electron donor-acceptor complex is developed. The method offers a mild and green approach for the synthesis of vinyl sulfones with excellent functional group compatibility under photocatalyst and oxidant-free conditions.

N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling

Two N-heterocyclic carbene ligands provide orthogonal chemoselectivity during the Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (≥10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium's ligation state during oxidative addition is different with SIMes compared to SIPr.

Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light

Transition-metal-catalyzed cross-couplings to construct C-C, C-O, and C-N bonds have revolutionized chemical science. Despite great achievements, these metal catalysts also raise certain issues including their high cost, requirement of specialized ligands, sensitivity to air and moisture, and so-called "transition-metal-residue issue". Complementary strategy, which does not rely on the well-established oxidative addition, transmetalation, and reductive elimination mechanistic paradigm, would potentially eliminate all of these metal-related issues. Herein, we show that aryl triflates can be coupled with potassium aryl trifluoroborates, aliphatic alcohols, and nitriles without the assistance of metal catalysts empowered by photoenergy. Control experiments reveal that among all common aryl electrophiles only aryl triflates are competent in these couplings whereas aryl iodides and bromides cannot serve as the coupling partners. DFT calculation reveals that once converted to the aryl radical cation, aryl triflate would be more favorable to ipso substitution. Fluorescence spectroscopy and cyclic voltammetry investigations suggest that the interaction between excited acetone and aryl triflate is essential to these couplings. The results in this report are anticipated to provide new opportunities to perform cross-couplings.

Palladium-Catalyzed Chemoselective Negishi Cross-Coupling of Bis[(pinacolato)boryl]methylzinc Halides with Aryl (Pseudo)Halides

We describe a palladium-catalyzed chemoselective Negishi cross-coupling of a bis[(pinacolato)boryl]methylzinc halide with aryl (pseudo)halides. This reaction affords an array of benzylic 1,1-diboronate esters, which can serve as useful synthetic handles f