672-36-6

Upstream product

• 882-33-7 diphenyldisulfane 
• 57644-86-7 Diphenyl-dithiophosphinsaere-phenylester 
• 5510-78-1 diphenylthiophosphinic acid-S-phenyl ester 
• 70562-38-8 triphenyl phosphorothionate 
• 4237-00-7 thiophosphoric acid O,O'-dimethyl ester S-phenyl ester 
• 98-80-6 phenylboronic acid 
• 1889-58-3 O,O-diethyl S-phenyl phosphorothioate 
• 203126-16-3 phenyltetrafluoro-λ⁶-sulfanyl chloride 
• 108-98-5 thiophenol 
• 1063625-79-5 trans-phenylsulfur chlorotetrafluoride 

Downstream Products

• 1207989-37-4 2-fluoroethyl benzenesulfinate 
• 203126-16-3 phenyltetrafluoro-λ⁶-sulfanyl chloride 
• 1207990-53-1 3-fluoro-1-phenylsulfinyl-pyrrolidine 
• 1207990-61-1 2-fluoromethyl-1-(phenylsulfinyl)pyrrolidine 
• 670-98-4 methyl benzenesulfinate 
• 350-50-5 benzyl fluoride 
• 136161-41-6 N-(2-fluoroethyl)-N-methylbenzenesulfonamide 
• 383-51-7 2-fluoroethyl benzenesulfonate 
• 1207990-32-6 N-(2-fluoroethyl)-N-methylbenzenesulfinamide 
• 2557-81-5 pentafluorosulfanylbenzene 
• 1063625-79-5 trans-phenylsulfur chlorotetrafluoride 
• 455-31-2 difluoromethylbenzene 
• 657-98-7 Benzolsulfinsaeurefluorid 

Relevant academic research and scientific papers

Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF 4Cl and Ar-SF 5Synthesis

In this manuscript we describe the oxidative fluorination of aryl phosphorothiolates to access Ar-SF4Cl compounds. These compounds serve as precursors for the highly coveted Ar-SF5 compounds. The use of phosphorothiolates as starting materials permits access to Ar-SF4Cl from a wide variety of available starting materials, namely boronic acids, diazonium salts, aryl iodides, thiophenols, or simple arenes. The protocol has been demonstrated for 10 examples and showed good tolerance to various functional groups. Finally, we demonstrated that AgBF4 can be used as a fluorinating agent, affording good yields of an Ar-SF5.

Enhanced preparation of aryl and heteryl sulfur pentafluorides using mercury (II) oxide - hydrogen fluoride media as a fluorinating reagent

We developed enhanced method for low temperature and good yield preparation of aryl and heteryl sulfur pentafluorides from chlorotetrafluorides using mercury oxide - hydrogen fluoride and mercury oxide - pyridinium poly(hydrogen fluoride) media as the fluorinating reagents.

Making the SF5 Group More Accessible: A Gas-Reagent-Free Approach to Aryl Tetrafluoro-λ6-sulfanyl Chlorides

Modern pentafluorosulfanyl (SF5) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl-SF4Cl compounds (key intermediates in state-of-the-art aryl-SF5 synthesis) that overco

Selective elemental fluorination in ionic liquids

Selective elemental fluorination in ionic liquids (ILs) will be presented as a new methodology. The tested reagents are organic disulphides and organic iodides. In addition, the stabilities of the ionic liquids [EMIM][(C 2F5)3PF3], [BMPL][(C 2F5)3PF3], [BMPL][OTf] and [BMPL][B(CN)4] against diluted fluorine (5 vol% in nitrogen) are investigated.

Arylsulfur chlorotetrafluorides as useful fluorinating agents: Deoxo- and dethioxo-fluorinations

Usage of arylsulfur chlorotetrafluorides 1 as versatile deoxo- and dethioxo-fluorinating agents is described. There have been developed two convenient methods for the in situ preparation of reactive arylsulfur trifluorides 2 from 1. The one is reduction of 1 with a reducer such as pyridine to 2, and the other is disproportionation of 1 with a diaryl disulfide to 2 with evolution of chlorine gas. The latter method is a convenient way to get neat 2 from 1. The in situ prepared 2 fluorinates many kinds of substrates such as alcohols, aldehydes, ketones, diketones, and carboxylic acids to give the corresponding CF, CF2, CF2CF2, and CF 3 compounds in high yields. 2 also fluorinates various sulfur compounds including CS groups to give CF2, OCF2, CF 3, and OCF3 compounds in high yields. Reactions of 2 with diols or bis(trimethylsilyl) derivatives of diols or amino alcohols provided the corresponding deoxofluoro-arylsulfinylation products in high yields. In addition, it has been found that chlorotetrafluorides 1 directly and effectively react with the sulfur compounds to give the corresponding fluoro compounds in high yields. Since they are the intermediates for the production of industrially useful arylsulfur pentafluorides, arylsulfur chlorotetrafluorides 1, in particular, phenylsulfur chlorotetrafluoride (1a) are expected to find use as inexpensive and versatile deoxo- and dethioxo-fluorinating agents for the preparation of many organofluoro compounds.

Arylsulfur trifluorides: Improved method of synthesis and use as in situ deoxofluorination reagents

Building on recent results of Umemoto and Winter, an improved method of synthesis of arylsulfur trifluorides, including the excellent, new deoxofluorination reagent Fluolead, is hereby reported. The method utilizes Br2 and KF as oxidizing and fluorinating reagents for efficient, high yield conversion of aryl disulfides and mercaptans to arylsulfur trifluorides. It has also been shown that both Fluolead and mesitylsulfur trifluoride may be generated in acetonitrile and used as in situ deoxofluorination reagents for conversion of either aldehydes or ketones to their respective gem-difluoro compounds. An analysis of the probable mechanism of action, including computational efforts, allows postulation of a rationale for the highly variable reactivities of different arylsulfur trifluorides as deoxofluorination reagents.

Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity

Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.

FLUORINATION PROCESSES WITH ARYLSULFUR HALOTETRAFLUORIDES

New fluorination processes for introducing one or more fluorine atoms into target substrate compounds with arylsulfur halotetrafluorides are disclosed. Also disclosed are methods for preparation of arylsulfur trifluorides.

A new method for the synthesis of organosulfur trifluorides

Simple, convenient and universal method of the different types of organosulfur trifluorides synthesis, with common formula RSF3 where R = dialkylamino group, aromatic or heterocyclic radical, was elaborated. The method consists in the reaction of thiosulf

Oxidative fluorination of S, Se and Te compounds

The synthesis and mechanism of formation of cis- and trans-Ph2SF4 is described. Starting compounds are Ph2S or Ph2SF2 and the oxidizing agent is XeF2 in the presence of Et4NCl. Also described is the synthesis of related chalcogen(IV and VI) fluorides such as t-butylSF3, difluorodibenzothiophene, PhSeF3, Ph2SeF2, PhSF5, p-MeC6H4SF5, PhSeF5, and PhTeF5. The reactions of Ph2S(O)F2 with alcohols and with the H2O-HF-glass system are briefly described.