4703-19-9

Usage

InChI:InChI=1/C19H17NO2S/c1-16-12-14-19(15-13-16)23(21,22)20(17-8-4-2-5-9-17)18-10-6-3-7-11-18/h2-15H,1H3

Upstream product

• 1483-73-4 diphenyliodonium bromide 
• 70-55-3 toluene-4-sulfonamide 
• 122-39-4 diphenylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4083-64-1 Tosyl isocyanate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1709-51-9 N,N-diphenylbenzenesulfonamide 
• 66003-76-7 Diphenyliodonium triflate 
• 68-34-8 phenyl toluenesulfonamide 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 71-43-2 benzene 
• 80-39-7 N-ethyl-4-methyl-benzenesulfonamide 
• 537-67-7 diphenylamine hydrochloride 

Downstream Products

• 122685-96-5 N,N-Diphenyl-2-benzoyl-4-methylbenzolsulfonamid 
• 122685-98-7 N,N-Diphenyl-4-methyl-2-(trimethylsilyl)benzolsulfonamid 
• 52914-18-8 phenyl-[2-(toluene-4-sulfonyl)-phenyl]-amine 
• 61654-49-7 Phenyl-[4-(toluene-4-sulfonyl)-phenyl]-amine 
• 122-39-4 diphenylamine 
• 55379-06-1 5-methyl-3-phenyl-1,2-benzisothiazole 1,1-dioxide 
• 122685-97-6 N,N-Diphenyl-2-chlor-4-methylbenzolsulfonamid 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 
• 3165-71-7 9-tosyl-9H-carbazole 
• 122685-95-4 N,N-Diphenyl-2-cyan-4-methylbenzolsulfonamid 
• 122685-92-1 5-methyl-3-p–tolylbenzo[d]isothiazole 1,1-dioxide 

Relevant academic research and scientific papers

DIARYL AMINE COMPOUND AND METHOD FOR PRODUCING THE SAME

The present invention relates to a process for the preparation of diaryl amine compounds. A compound represented by chemical formula 1, a compound represented by chemical formula 2, and a synthetic reagent in a solvent, the synthetic reagent being CsF, KF, 18 - crown -6, K. 2 CO3, [TBAT] The present invention relates to a process for the preparation of diaryl amine compounds comprising a material selected from the group consisting of a (tetrabutylammonium difluorotriphenylsilicate), TBAF (tetrabutylammonium fluoride) and combinations thereof. Chemical Formula 1. Chemical Formula 2. The diaryl amine compound can be synthesized under the absence of a transition metal to be used to synthesize diaryl amine compounds having various substituents.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor

Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring

Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).

Transition-Metal-Free Diarylation of Isocyanates with Arynes

A facile method for the transition-metal-free diarylation of isocyanates with arynes in the presence of cesium fluoride has been developed, which affords functionalized diaryl amines in moderate to excellent yields. This reaction has good functional group tolerance and provides excellent regioselectivity by utilizing a methoxy-substituted aryne precursor.

Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion

A silica-supported ionic liquid phase catalyst containing Keggin-type anion has been prepared by covalent grafting of ferrocene-tagged ionic liquid in a matrix of silica followed by anion metathesis reaction. This novel catalyst served as a robust heterogeneous catalyst for the synthesis of biologically active sulfonamides from 4-toluenesulfonyl chloride and amines. Additionally, recycling experiments showed that the catalyst could be reused five times.

Copper-catalyzed N-arylation of tert-butyl N-sulfonylcarbamates with diaryliodonium salts at room temperature

A new and mild synthetic approach for the synthesis of N-arylsulfonamides under copper-catalyzed conditions at room temperature has been developed. The reaction employs various tert-butyl N-sulfonylcarbamates and diaryliodonium salts to avoid potential genotoxic impurities. A one-pot coupling/Boc-deprotection sequence is also reported to provide mono N-arylsulfonamides in good to excellent yields.

Ultrasound-promoted green approach for the synthesis of sulfonamides using natural, stable and reusable Natrolite nanozeolite catalyst at room temperature

Natural Natrolite nanozeolite has been investigated as an efficient and reusable catalyst for the N-sulfonylation of amines under ultrasound irradiation at room temperature. Compared with traditional methods, the significant advantages for method are green solvent, milder and cleaner conditions, higher purity and yields, shorter reaction time, easier work-up procedure and the lower generation of waste or pollutions. The catalyst can be recovered and reused several times without significant loss of its catalytic activity.

Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams

The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.

Copper-catalyzed direct N-arylation of N-arylsulfonamides using diaryliodonium salts in water

An efficient copper-catalyzed N-arylation of N-arylsulfonamides with diaryliodonium salts is reported. The reaction employs diaryliodonium salts and N-arylsulfonamides in water at room temperature, giving the products in moderate to excellent yields.