66107-36-6

Usage

Uses

Used in Organic Synthesis:
2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for its high reactivity, enabling various chemical reactions in the synthesis of complex organic compounds.
Used in Peptide Synthesis:
In the pharmaceutical industry, 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE is used as a coupling agent to facilitate the formation of peptide bonds, which is crucial for the production of peptide-based drugs.
Used in Pharmaceutical Production:
2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE is used as an intermediate in the development and manufacturing of pharmaceuticals, contributing to the creation of new and effective medications.
Used in Agrochemical Production:
2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE is also utilized in the production of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Used as a Protecting Group in Organic Chemistry:
2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE serves as a protecting group for alcohols during organic synthesis, preventing unwanted side reactions and facilitating selective reactions.

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

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 95-57-8 2-monochlorophenol 
• 1493-13-6 trifluorormethanesulfonic acid 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 28036-18-2 2-Chlorphenylphosphonsaeurediethylester 
• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 19493-31-3 2-chloro-2'-methyl-1,1'-biphenyl 
• 27594-20-3 N,N,N',N'-Tetraisopropyl-m-phenylenediamine 
• 349537-53-7 1-acetylamino-1-(2'-chlorophenyl)ethene 
• 1207669-18-8 tert-butyl [2-(2-chlorophenyl)prop-2-en-1-yl]carbamate 
• 17763-67-6 Phenyl triflate 
• 1393539-03-1 2-(o-chlorophenyl)-1-octene 
• 2051-60-7 2-chloro-1,1'-biphenyl 
• 87170-05-6 1-chloro-2-pentylbenzene 
• 100634-68-2 1-chloro-2-undecylbenzene 
• 18434-12-3 1,2-diphenyl-1H-indole 

Relevant academic research and scientific papers

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.

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.

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.

Tandem thia-Fries rearrangement-cyclisation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate benzyne precursors

A novel transformation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate aryne precursors is described. The Royal Society of Chemistry.

Intermolecular mizoroki-heck reaction of aliphatic olefins with high selectivity for substitution at the internal position

New ligand for old reaction: The title reaction of aryltriflates with aliphatic olefins leads to substitution at the internal position with high selectivity. The ratio of the desired isomer (shown in the scheme) to the sum of all other isomers is generall

Palladium-catalyzed desulfitative arylation by C-O bond cleavage of aryl triflates with sodium arylsulfinates

An efficient Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates as arylation reagents by C-O bond cleavage of aryl triflates was developed. With only 2 mol % of Pd(OAc)2 as catalyst and XPhos as ligand, the reaction proceeded well for a range of substrates.

A novel approach to 3-methylindoles by a heck/cyclization/isomerization process

Chemical Equation presented A novel synthesis of 3-methyllndoles from chlorotrlflates through a Heck reaction, carbamate/aryl chloride coupling, and Isomerlzatlon sequence Is presented. The three-step sequence Is highly efficient and general, enabling the

Synthesis of hydroxylated oligoarene-type phosphines by a repetitive two-step method

Hydroxylated oligoarene-type phosphines with various substitution patterns were synthesized. Such phosphines have potential as ligands for transition metal-catalyzed reactions. A successful route, which includes a repetitive Suzuki-Miyaura coupling-triflation sequence, reduction, and salt formation, was established starting from 2-bromophenyldicyclohexylphosphine oxide. Other key aspects of the method are the use of suitable triflation reagents and the formation of phosphines as HBF4 salts. Interesting information was obtained from careful analysis of the byproducts in the triflation and reduction steps, and the mechanisms for their formation were proposed.

Low-Temperature Ag/Pd-catalyzed decarboxylative cross-coupling of aryl trflates with aromatic carboxylate salts

Chemical Equation Presented At 50°C lower than the best known copper catalysts, a catalytic silver(I)/ palladium(II) system allows the decarboxylative cross-coupling of arenecarboxylates with aryl triflates at temper-atures as low as 120°C. Remarkably, polychlorinated and many heterocyclic arenecarboxylates are converted for the first time in high yields. FG = functional group.

Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process

A detailed study of the scope of a new Pd-catalyzed synthesis of indolesfrom 1,2-dihaloarenes and o-halobenzene sulfonates and imines is descri bed. The cascade reaction comprises an imine a-arylation ollowed by an intramolecular C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N-H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularlyappropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precur sors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.