351186-41-9

Upstream product

• 4319-49-7 1-aminomorpholine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-49-0 p-toluidine 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 100-63-0 phenylhydrazine 
• 18412-57-2 p-tolyltriethoxysilane 
• 18056-92-3 diethoxy(di-4-methylphenyl)silane 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 36301-60-7 4-aminomorpholine sulfur dioxide complex 
• 106-38-7 para-bromotoluene 

Downstream Products

• 51751-71-4 1-methyl-4-(propane-2-sulfonyl)benzene 
• 31536-21-7 isopropyl 4-methylbenzenesulfinate 
• 5395-20-0 1-methyl-4-(benzylsulfonyl)benzene 
• 41571-21-5 N-morpholino-1-phenylmethanimine 
• 74320-07-3 1-(4-methylphenylsulfonyl)-hexane 
• 74698-01-4 hexyl p-toluenesulfinate 
• 90926-25-3 1-(4-tolylsulfonyl)propane 
• 114376-01-1 propyl 4-methylbenzenesulfinate 
• 3185-99-7 Methyl p-tolyl sulfone 
• 640-57-3 phenyltolylsulfone 
• 5535-52-4 tolyl vinyl sulfone 
• 858492-12-3 α-(toluene-4-sulfonyl)-isobutyric acid ethyl ester 

Relevant academic research and scientific papers

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO2 Source

A convenient synthesis of DABCO·(SO2)2 (abbreviated as DABSO) is reported. Using a two-chamber setup, sulfur dioxide is generated in one chamber and consumed in the other. This closed system overcomes safety issues related to working

Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium Salts with Sulfur Dioxide and Hydrazines

A photoredox-catalyzed three-component synthesis of N-aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy-to-handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium salt as convenient source for aryl radicals. (Figure presented.).

Palladium-catalyzed aminosulfonylation of aryl iodides by using Na 2SO3 as the SO2 source

We realized an interesting palladium-catalyzed aminosulfonylation of aryl iodides by using Na2SO3 as a cheap SO2 source. In most cases, the yields were comparable to those reported by using the 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABCO·2SO 2, DABSO) as the SO2 source. Copyright

A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines

A three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate is reported, leading to N-aminosulfonamides in good yields. Not only triethoxy(aryl)silanes but also triethoxy(alkyl)silanes are compatible during the process of insertion of sulfur dioxide. Additionally, diethoxydiarylsilanes are suitable under the conditions as well.

Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source

Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.

Aminosulfonylation of aromatic amines, sulfur dioxide and hydrazines

A facile route to aryl N-aminosulfonamides under mild conditions is provided. The reaction of aromatic amines (including heteroaromatic amines), sulfur dioxide, and hydrazines proceeds efficiently with good functional group tolerance. The in situ generated diazonium ion is involved in the aminosulfonylation process. This journal is the Partner Organisations 2014.

Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO×(SO2)2 and hydrazines

The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO 2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional-group tolerance. A radical process is proposed for this transformation. The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds under mild reaction conditions, is fast, has a broad substrate scope, and gives the products in high yiels (21 examples). A plausible mechanism that involves a radical process is also proposed. Copyright

One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.

A palladium-catalyzed reaction of aryl halides, potassium metabisulfite, and hydrazines

Aryl N-aminosulfonamides could be easily produced via a palladium-catalyzed coupling of aryl halides, potassium metabisulfite, and hydrazines. Potassium metabisulfite is an excellent equivalent of sulfur dioxide in the reaction of palladium-catalyzed aminosulfonylation. The Royal Society of Chemistry 2012.