132993-23-8

Basic information

• Product Name: 4-fluorophenyl trifluoromethanesulfonate
• Synonyms: 4-fluorophenyl trifluoromethanesulfonate
• CAS NO: 132993-23-8
• Molecular Weight: 244.167
• Mol File: 132993-23-8.mol

Chemical Properties

• CAS DataBase Reference: 4-fluorophenyl trifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluorophenyl trifluoromethanesulfonate(132993-23-8)
• EPA Substance Registry System: 4-fluorophenyl trifluoromethanesulfonate(132993-23-8)

Safety Data

• Hazardous Substances Data: 132993-23-8(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 135-19-3 β-naphthol 
• 371-41-5 4-Fluorophenol 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 462-06-6 fluorobenzene 
• 324-74-3 4-fluoro-biphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 450-39-5 4-(4-fluorophenyl)anisole 
• 489434-07-3 1-(1-butoxy-vinyl)-4-fluoro-benzene 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 16547-13-0 4-fluoro-N-methyl-N-phenylbenzylamine 
• 101125-32-0 3-(4-fluorophenyl)-1H-indole 
• 399-10-0 4'-fluorochalcone 
• 3575-80-2 melperone 
• 52-86-8 haloperidol 
• 72358-74-8 4-fluoro-o-phenyl phenyl(phenyl)phosphinate 
• 38695-26-0 1-(4-fluorobenzyl)-4-methoxybenzene 
• 1151856-21-1 3-(4-fluorophenyl)-3-methylindoline 

Relevant articles and documents

Benzothiazol-2-yl(difluoro)methanesulfonic acid: Synthesis and reactions

The condensation of o-aminothiophenol with sulfodifluoroacetic acid led to the formation of benzothiazol-2-yl(difluoro)methanesulfonic acid whose aryldiazonium salts were converted by pyrolysis into aryl benzothiazol-2- yl(difluoro)methanesulfonates. Nauka/Interperiodica 2006.

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

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.

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

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.

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.

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

Directed ortho Metalation (D o M)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study

A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (D o M) is reported. In general, the Suzuki-Miyaura and Negishi protocols show gre