146397-87-7

Usage

Uses

Used in Pharmaceutical Industry:
Methanesulfonic acid, 1,1,1-trifluoro-, 4-(trifluoromethyl)phenyl ester is used as a reactant for the design of PHOX ligands, which are essential in the synthesis of pharmaceutical agents requiring single enantiomers. It plays a crucial role in asymmetric Heck reactions, a type of chemical reaction that produces chiral molecules with a specific three-dimensional arrangement.

InChI:InChI=1/C8H4F6O3S/c9-7(10,11)5-1-3-6(4-2-5)17-18(15,16)8(12,13)14/h1-4H

Upstream product

• 540-38-5 p-Iodophenol 
• 402-45-9 4-hydroxybenzotrifluoride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 2926-30-9 sodium triflate 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 109586-39-2 4-iodophenyl trifluoromethanesulfonate 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 1174000-61-3 4-(methoxycarbonyl)-2,6-bis(4-(trifluoromethyl)phenyl)pyridine 1-oxide 
• 1499187-62-0 (1S,4S)-methyl 4-(p-trifluoromethylphenyl)cyclopent-2-ene-1-carboxylate 
• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 
• 944351-60-4 1-(4-trifluoromethyl-phenyl)-cyclohexanecarbonitrile 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 53451-87-9 phenyl(4-trifluoromethylphenyl)amine 
• 1127562-66-6 C₁₁H₈F₃NOS 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 98-08-8 α,α,α-trifluorotoluene 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 402-45-9 4-hydroxybenzotrifluoride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 61062-55-3 2-phenyl-1-(4-(trifluoromethyl)phenyl)ethan-1-one 

Relevant academic research and scientific papers

On the preparation of ortho-trifluoromethyl phenyl triflate

In contrast to an earlier report advocating a copper-mediated trifluoromethylation of ortho-iodophenyl triflate, ortho-trifluoromethyl phenyl triflate may be prepared simply by reacting the corresponding phenol with triflic anhydride in the presence of a

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.

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.

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.

Solvent-free ruthenium-catalysed triflate coupling as a convenient method for selective azole-o-C-H monoarylation

Metal-catalysed ortho-directed C-H functionalization usually faces selectivity issues in the competition between mono- and disubstitution processes. We report herein the ruthenium-catalysed N-directed C-H monoarylation of arylpyrazoles with a selectivity

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

Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling

Catalytic enantioselective conjunctive cross-coupling has been developed to construct tertiary alkylboronic esters. These reactions occur with good yield and enantioselectivity for a range of substrates. Mechanistic experiments reveal aspects of the catalytic cycle that allow hindered substrates to react without significant complicating side reactions.

A Stereoselective Reductive Hosomi-Sakurai Reaction

A novel reductive variant of the classical Hosomi-Sakurai reaction is reported. This transformation hinges on a redox-neutral, stereoselective internal reduction event under mild conditions. This operationally simple reaction relies on readily available starting materials and leads to useful products in diastereoselectivities of up to 7:1. The versatility of this new method is demonstrated through the stereoselective one-step synthesis of an AChE inhibitor.

Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron “Ate” Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables “ate” complex formation and overcomes catalytic inhibition by halide ions.

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents

Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.