444-31-5

Upstream product

• 7789-21-1 fluorosulphonic acid 
• 108-88-3 toluene 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 143893-31-6 potassium toluenesulfonate 
• 15898-37-0 sodium 2-methylbenzenesulfinate 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 137-06-4 2-thiocresol 
• 368-43-4 phenylsulfonyl fluoride 
• 74-88-4 methyl iodide 

Downstream Products

• 4430-23-3 3H-benzo[c][1,2]oxathiole-1,1-dioxide 
• 96892-87-4 3-(2-Fluorosulfonyl-benzyl)-2-methyl-benzenesulfonyl fluoride 
• 643-58-3 2-methylbiphenyl 
• 91340-63-5 N-(2-methylphenylsulfonyl)-N-(tert-butyl)amine 

Relevant academic research and scientific papers

Synthesis of Sulfonyl Fluorides from Sulfonamides

A simple and practical synthesis of sulfonyl fluorides from sulfonamides is reported. The method capitalizes on the formation of the sulfonyl chloride by virtue of the reaction of Pyry-BF4 and MgCl2, and subsequent in situ conversion to the more robust and stable sulfonyl fluoride by the presence of KF. The mild conditions and high chemoselectivity of the protocol enable the late-stage formation of sulfonyl fluorides from densely functionalized molecules.

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Sulfur fluoride exchange (SuFEx) has emerged as the new generation of click chemistry. We report here a SuFEx-enabled, agnostic approach for the discovery and optimization of covalent inhibitors of human neutrophil elastase (hNE). Evaluation of our ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride. Synthetic derivatization of the initial hit led to a more potent agent, 2-(fluorosulfonyl)phenyl fluorosulfate with IC50 0.24 μM and greater than 833-fold selectivity over the homologous neutrophil serine protease, cathepsin G. The optimized, yet simple benzenoid probe only modified active hNE and not its denatured form.

Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates

Studies on directed ortho -metalation (DoM) of arenesulfonyl fluorides (ArSO 2 F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, -78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO 2 F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO 2 F) display fragmentation to arynes and migration of the SO 2 F group to the ortho position (anionic thia-Fries rearrangement).

Sulfur(VI) fluoride compounds and methods for the preparation thereof

This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.

Orthoamides, LXIV [1]. Formylation of aromatic compounds by tris(dichloromethyl)amine and oligoformylamine derivatives in the presence of superacids

Tris(dichloromethyl)amine (4), triformamide (1) and tris(diformylamino) methane ( formyl-aalen ) (2) can be activated by addition of trifluoromethanesulfonic acid. The formylating systems thus formed transform activated aromatic compounds, such as toluene, anisole or 2,4-dimethoxybenzene to the corresponding aldehydes. The formylating ability of systems from 4 and superacids, such as FSO3H, FSO3H/SbF5, C 4F9SO3H, and mixtures of aluminum chloride with C4F9SO3H and chlorosulfonic acid, respectively, is compared. In general, low reaction temperatures (-20 to -10°C) are necessary to obtain aldehydes with acceptable to good yields. Remarkably, at higher temperatures (～ 100°C) compound 4 can also act as a formylating agent in the presence of suitable zeolites, as e. g. zeolite HBEA. Reaction mechanisms of the new formylation reactions are proposed.

NOVEL COMPOUNDS

The present invention relates to novel indole derivatives such as compounds of the formula (I): which possess antagonist potency at the 5-HT6 receptor and the use of such compounds or pharmaceutically acceptable salts or solvates thereof in the treatment of Alzheimer's disease and other CNS disorders.

OXIDATION OF METHYL-SUBSTITUTED BENZENESULFONYL FLUORIDES IN THE PbO2-HSO3F SYSTEM

The transformations of the sulfonyl fluorides of methyl-substituted benzenes in the PbO2-HSO3F system were studied.They take place through a stage involving the one-electron oxidation of the substrate to aromatic radical-cations.One of the transformation paths of the latter is realized through the elimination of a proton from the methyl groups involved to the greatest degree in the delocalization of the unpaired electron.This leads to the formation of diarylmethanes and the fluorosulfonates of substituted benzyl alcohols, which give substituted tolylsultones and benzyl alcohols during hydrolysis of the acid solution and methyl ethers of benzyl alcohols during methanolysis.The other path, which arises during localization of the unpaired electron in the unsubstituted positions of the benzene ring, leads to biaryls.

KINETIC INVESTIGATION OF THE S-FLUORINATION OF ARENESULFINATES WITH PERCHLORYL FLUORIDE

The effect of substituents and solvents on the kinetics of S-fluorination of sodium arenesulfinates with perchloryl fluoride was investigated.Alternative fluorination mechanisms were examined, and it was found that the mechanism is SN2 substitution at the fluorine atom.