17763-67-6

Usage

Uses

Used in Chemical Synthesis:
Phenyl trifluoromethanesulfonate is used as an arylating agent for the asymmetric α-arylation of ketones, catalyzed by Pd(dba)2 and difluorphos. This application is significant in the synthesis of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, phenyl triflate is used as a reactant in the one-pot synthesis of carbazoles. This process involves palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling, which is crucial for the development of new drugs and therapeutic agents.
Used in Organic Chemistry Research:
Phenyl triflate is utilized in the synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of a palladium-based catalyst. This application is essential for the development of novel organic compounds with potential applications in various fields.
Used in Synthesis of Chiral Compounds:
Phenyl trifluoromethanesulfonate is employed as an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran. This process is vital for the production of chiral compounds, which are crucial in the pharmaceutical and chemical industries for their unique properties and applications.

Preparation

Synthesis of Phenyl trifluoromethanesulfonate: The reaction of phenol (1.00 g, 10.6 mmol) with triflic anhydride as outlined in the general procedure provided phenyl trifluoromethanesulfonate as colorless oil (0.73 g, 30%).1H NMR (400 MHz, CDCl3) δ 7.50 – 7.42 (m, 2H), 7.41 – 7.36 (m, 1H), 7.32 – 7.24 (m, 2H).

InChI:InChI=1/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H

Upstream product

• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 1529-17-5 phenyltrimethylsilyl ether 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 108-95-2 phenol 
• 1493-13-6 trifluorormethanesulfonic acid 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 63028-10-4 cyclohexa-2,4-dienyl trifluoromethanesulfonate 
• 153688-92-7 3-iodophenyl trifluoromethanesulfonate 
• 617-86-7 triethylsilane 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 288-32-4 1H-imidazole 
• 29540-81-6 1-(trifluoromethylsulfonyl)-1H-imidazole 

Downstream Products

• 124244-39-9 (-)-(S)-2,5-dihydro-2-phenylfuran 
• 191427-03-9 (S)-2-phenyl-2,3-dihydrofuran 
• 131516-05-7 (R)-2-phenyl-2,3-dihydrofuran 
• 175274-01-8 (R)-2-phenyl-2,5-dihydrofuran 
• 2189-60-8 Octylbenzene 
• 36586-17-1 (E)-(2-butoxyethenyl)benzene 
• 56750-84-6 (1-butoxyethenyl)benzene 
• 98-86-2 acetophenone 
• 145372-92-5 4-phenyl-4H-1,3-dioxin 
• 122-78-1 phenylacetaldehyde 
• 129126-31-4 (Z)-N,N-dimethyl-2-(styryloxy)ethanamine 
• 129126-30-3 (E)-N,N-dimethyl-2-(styryloxy)ethanamine 
• 129126-51-8 N,N-dimethyl-2-[(1-phenyl)ethenyloxy]ethanamine 
• 60676-51-9 methyl (Z)-2-(acetylamino)-3-phenylpropenoate 

Relevant academic research and scientific papers

Dual Photoredox-/Palladium-Catalyzed Cross-Electrophile Couplings of Polyfluoroarenes with Aryl Halides and Triflates

A visible-light photoredox-/Pd-catalyzed cross-electrophile arylation of polyfluoroarenes with aryl halides and triflates in the presence of dialkylamines is reported for the first time. This synergistic protocol affords access to a series of fluorodiaryls from easily available starting materials under mild and operationally simple conditions. A series of mechanistic experiments, including the stoichiometric reactions of a ligated (aryl)Pd complex, Stern-Volmer fluorescence quenching studies, cyclic voltammetry studies, and UV-vis spectroscopy, were performed to elucidate the potential catalytic pathway in this synergistic process.

Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a C - C Bond Cleavage

Herein, we first present a nickel-catalyzed arylation and alkenylation of tert-cyclobutanols with aryl/alkenyl triflates via a C-C bond cleavage. An array of γ-substituted ketones was obtained in moderate-to-good yields, thus featuring earth-abundant nick

Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones

A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.

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.

Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates

This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.

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.

Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage

A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t

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.

Reductive Coupling between C-N and C-O Electrophiles

The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been studied. Preliminary mechanistic studies revealed that the benzyl ammoniums were activated through a radical mechanism.

METAL-FREE DIRECT ARYLATION OF DIALKYL PHOSPHONATES FOR THE SYNTHESIS OF MIXED ALKYL ARYL PHOSPHONATES

Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This