1263276-85-2

Upstream product

• 825-83-2 4-trifluoromethylbenzenethiol 
• 68-12-2 N,N-dimethyl-formamide 
• 103-83-3 N,N'-dimethylbenzylamine 
• 2991-42-6 4-trifluorophenylsulfonyl chloride 
• 830-43-3 4-(trifluoromethyl)benzenesulfonamide 
• 616-38-6 carbonic acid dimethyl ester 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 124-40-3 dimethyl amine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 

Downstream Products

• 599-69-9 N,N,4-trimethylbenzenesulfonamide 
• 88584-49-0 4-(fluoromethyl)-N,N-dimethylbenzenesulfonamide 
• 1282034-12-1 N-butyl-N-methyl-4-(trifluoromethyl)benzenamine 
• 113845-68-4 1-(4(-trifluoromethyl)phenyl)pyrrolidine 

Relevant academic research and scientific papers

Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light

An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.

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.

Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines

A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).

Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides

By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.

Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists.

N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate

Abstract: Dimethyl carbonate (DMC), an environmentally friendly methylation agent, is a substitute for traditional methylation agents such as methyl halides (CH3X, X?=?I, Br, Cl) or dimethyl sulfate. An efficient, convenient, and green method has been developed for N-methylation of poorly nucleophilic aromatic amines with DMC. It was found that the couple PEG400/K2CO3 provides good selectivity for the N-methylation product. Finally, the mechanism for reaction of amines with DMC was investigated, and a plausible multistep mechanism proposed and verified. Graphical Abstract: [Figure not available: see fulltext.]

Copper-mediated S-N formation via an oxygen-activated radical process: A new synthesis method for sulfonamides

Copper-mediated direct S-N formation using readily available starting materials via an oxygen-activated radical process has been developed. This method provides a novel and direct approach for synthesis of sulfonamides under air conditions. the Partner Organisations 2014.

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.