68253-25-8

Upstream product

• 1535-35-9 4-fluorobenzenesulphenyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 371-42-6 4-Fluorothiophenol 

Downstream Products

• 1044572-84-0 4-((4-fluoro-2-(phenylethynyl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 1044572-85-1 4-((5-fluoro-4'-methoxy-[1,1'-biphenyl]-2-yl)sulfinyl)-N,N-dimethylaniline 
• 1044573-06-9 {4-[4-chloro-2-(4-chlorophenylsulfanyl)benzenesulfinyl]phenyl} dimethylamine 
• 1309446-21-6 2'-((4-(dimethylamino)phenyl)sulfinyl)-5'-fluoro-[1,1'-biphenyl]-4-carbonitrile 
• 1309446-22-7 4-((5-fluoro-4'-methoxy-[1,1'-biphenyl]-2-yl)sulfinyl)-N,N-dimethylaniline 
• 1309446-23-8 4-((4-fluoro-2-(pent-1-yn-1-yl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 1309446-24-9 2-((4-(dimethylamino)phenyl)sulfinyl)-5-fluorobenzonitrile 

Relevant academic research and scientific papers

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.

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.