68253-26-9

Upstream product

• 63029-16-3 (4-amino-phenyl)-(4-dimethylamino-phenyl)-sulfide 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 
• 2751-25-9 p-chlorophenylsulfonyl hydrazide 
• 121-69-7 N,N-dimethyl-aniline 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 22865-51-6 4-dimethylamino-4'-nitrodiphenyl sulfide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 106-54-7 p-Chlorothiophenol 

Downstream Products

• 1044572-72-6 [4-(4-chloro-benzenesulfinyl)phenyl]dimethylamine 
• 1044572-81-7 5'-chloro-2'-((4-(dimethylamino)phenyl)sulfinyl)-[1,1'-biphenyl]-4-carbonitrile 
• 1309446-19-2 4-((4-chloro-2-(phenylethynyl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 1309446-20-5 4-((4-chloro-2-((trimethylsilyl)ethynyl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 1309446-37-4 ethyl 2-(4-chloro-2-((trimethylsilyl)ethynyl)benzyl)acrylate 

Relevant academic research and scientific papers

Electrochemical access to aryl sulfides from aryl thiols and electron-rich arenes with the potassium iodide as a mediator

An indirect electrooxidation method catalyzed by potassium iodide at a low potential for the synthesis of aryl sulfides from aryl thiols and electron-rich arenes has been developed. Cyclic voltammetry was carried out to investigate the electrocatalytic ac

Sodium Iodide (NaI)-Catalyzed Cross-Coupling for C?S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides

A simple and practical NaI-catalyzed direct C?H sulfenylation of arenes has been developed under air. In this reaction, aryl sulfides were obtained in moderate to excellent yields with high regioselectivity from readily available aromatic compounds and aryl/alkyl thiols, even on gram scale. To demonstrate the practicability of this reaction, two bioactive compound skeletons were synthesized in good yields. This method can also be used to late-stage modification of curcumin.

Electrocatalytic Oxidant-Free Dehydrogenative C?H/S?H Cross-Coupling

An environmentally friendly electrocatalytic protocol has been developed for dehydrogenative C?H/S?H cross-coupling. This method enabled C?S bond formation under catalyst- and oxidant-free conditions. Under undivided electrolysis conditions, various aryl/heteroaryl thiols and electron-rich arenes afforded the C?S bond-formation products in 24–99 % yield. A preliminary mechanistic study indicated that the generation of aryl radical cation intermediates is key to the success of this transformation.

Odorless, Regioselective Synthesis of Diaryl Sulfides and α-Thioaryl Carbonyls from Sodium Arylsulfinates via a Metal- Free Radical Strategy in Water

Regioselective arylthiolations of aromatic amines, arenols and ketones via C–H bond functionalization have been achieved with I2and PPh3in an aqueous system, whereby arylsulfenyl radicals are in situ generated from odorless sodium arylsulfinates. The arylsulfenyl radicals can react with free anilines containing electron-withdrawing groups and complex substrates (estrone and progesterone). Further experiments and quantum chemical calculations were also performed to deduce a mechanism for the formation of arylsulfenyl radicals. (Figure presented.).

Iodine-Mediated Synthesis of Aromatic Thioethers with Aromatic Amines and Sulfonyl Hydrazides in High Regioselectivity via C(sp2)-H Bond Functionalization

An iodine-mediated synthesis of aromatic thioethers from aromatic amines and sulfonyl hydrazides via C(sp2)-H bond functionalization and C-S bond formation has been developed. In this procedure, various substituents on the sulfonyl hydrazides, such as alkyl, methoxyl, chloro, bromo and fluoro groups, and aromatic amines are tolerated in the thiolation which generates the desired products in moderate to good yields.

Iodine catalyzed cross-dehydrogenative C-S coupling by C(sp2)-H bond activation: Direct access to aryl sulfides from aryl thiols

A novel, efficient and unprecedented green protocol for the formation of C-S bonds has been developed under metal-free conditions. This protocol involves the synthesis of aryl sulfides through the cross-dehydrogenative coupling of readily available aryl t

Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide-magnesium exchange

The aryl sulfoxide moiety allows an expedient two-step difunctionalisation of readily available diaryl sulfoxides. Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes (furans, thiophenes, benzofurans and pyridines) were prepared in a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metallation-directing group, allowing smooth ortho-magnesiation with TMPMgCl.LiCl (TMP=tetramethylpiperidine). After a quenching reaction with an electrophile, the resulting sulfoxide is converted into a second magnesium reagent with iPrMgCl.LiCl (sulfoxide-magnesium exchange), which can be trapped with various electrophiles. Highly chemoselective TMPMgCl.LiCl and iPrMgCl.LiCl are compatible with a broad range of functional groups (e.g., F, Cl, CF 3, CN, CO2tBu, alkynyl, ethers, thioethers). Large-scale reactions (25-40 mmol) and the preparation of fully functionalised furans and thiophenes are also reported. Successful exchange: Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes were prepared in a two-step sequence, triggered by an aryl sulfoxide group. The chemoselective reagents used, TMPMgCl.LiCl (TMP=tetramethylpiperidine) and iPrMgCl.LiCl, are compatible with a broad range of functional groups (see scheme; E=electrophile.)

Meta- and para-difunctionalization of arenes via a sulfoxide-magnesium exchange reaction

(Chemical Equation Presented) The aryl sulfoxide moiety (ArSO) allows an expedient two-step meta-, para-difunctionalization of readily available diaryl sulfoxides. In the first step, the sulfoxide plays the role of a directing metalation group. In the second step, triggered by i-PrMgCl·LiCl, it becomes a leaving group and undergoes a regioselective sulfoxide-magnesium exchange.