2715-05-1

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 2715-07-3 (3-trifluoromethyl-phenyl)-phenyl sulfide 
• 114650-56-5 C₁₃H₉F₃N₂S 
• 401-94-5 3-nitro-5-(trifluoromethyl)-phenylamine 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 1330786-68-9 (3-trifluoromethylphenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate 
• 873-55-2 sodium benzenesulfonate 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 66003-76-7 Diphenyliodonium triflate 
• 591-51-5 phenyllithium 
• 71-43-2 benzene 
• 16883-74-2 lithium benzenesulfinate 
• 1121974-62-6 C₇H₄F₃O₂S^(1-)*Li⁽¹⁺⁾ 
• 108-98-5 thiophenol 

Relevant academic research and scientific papers

Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates

A novel nickel-catalyzed cross-coupling of sulfinic acid salts with aryl halides is described. The reaction provides access to various diaryl sulfones in moderate to excellent yields. A broad range of functional groups and heteroaromatic compounds is tolerated under the reaction conditions.

Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides

An efficient cross-coupling of sodium or lithium sulfinates with aryl iodides, using a combination of nickel and photoredox catalysis, is described. The dual catalyst system enables a versatile synthesis of aryl sulfones at room temperature in good yields and displays a broad functional group compatibility. The potential utility of this method in the late-stage diversification of complex molecules and in the conversion of organolithium reagents and sulfur dioxide into sulfones is demonstrated.

One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts

A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the organometallic compound, sulfinate formation, and arylation) leads to a one-pot sequence for the synthesis of aryl sulfones from simple starting materials. The chemoselectivity of unsymmetrical diaryliodonium salts has been investigated. Potential and limitations of this method will be discussed.

Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts

An efficient, high-yielding, and transition-metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts has been developed. The mild reaction conditions tolerate a range of functional groups, and unsymmetrical diaryliodonium salts show high chemoselectivity.

Arylation of lithium sulfinates with diaryliodonium salts: A direct and versatile access to arylsulfones

An efficient, transition-metal-free arylation of lithium sulfinates, which are readily accessible from reactions of organolithium reagents with sulfur dioxide, is described. Based on this method, a practical protocol for the direct transformation of (hetero)arenes and (hetero)aromatic halides into diarylsulfones was developed.

A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES

Properly substituted diazosulfides XC6H4-N=N-SPh (1) (either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2).Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3- or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeCO, 3-MeO, 4-NO2, 4-PhCO, and 4-PhSO2.For different reasons, the reaction practically fails as a useful nitrile synthesis when X= H, 4-MeO, 2-, or 3-NO2.The collected evidences agree well with the intervention of an SRN1 mechanism to which diazosulfides 1, given their easy reducibility followed by a prompt fragmentation of the C-N and N-S bonds, are convenient participating substrates.An important consequence of the mechanism involved is the behaviour of bromo and chloro derivatives (1: X= Br, Cl) which lead, through the contemporaneous introduction of two cyano functionalities, to more than satisfactory yields of the corresponding dicyanobenzenes.