90309-29-8

Upstream product

• 371-42-6 4-Fluorothiophenol 
• 121-69-7 N,N-dimethyl-aniline 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 

Downstream Products

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

Relevant academic research and scientific papers

Nitrosoarene-catalyzed regioselective aromatic C-H sulfinylation with thiols under aerobic conditions

Aromatic amines and (hetero)arenes, such as indoles and pyrroles, are regioselectively sulfinylated under mild aerobic conditions using nitrosoarenes as a redox-catalyst. The nitrosoarene is involved in the electron transfer process with arenes to generate a crucial arene radical cation intermediate for C-H sulfinylation. The present methodology requires no directing group, can be scaled up easily and is applicable for the late-stage functionalization of drug molecules and natural products with high regioselectivity.

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.)