1044572-72-6

Upstream product

• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 26760-21-4 methyl p-chlorobenzenesulphinate 
• 121-69-7 N,N-dimethyl-aniline 
• 106-54-7 p-Chlorothiophenol 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 68253-26-9 4-(4-chlorophenylthio)-N,N-dimethylbenzenamine 

Downstream Products

• 1044572-82-8 [4-(4'-bromo-5-chlorobiphenyl-2-sulfinyl)phenyl]dimethylamine 
• 1044572-81-7 5'-chloro-2'-((4-(dimethylamino)phenyl)sulfinyl)-[1,1'-biphenyl]-4-carbonitrile 
• 1044572-83-9 5-chloro-2-(4-dimethylamino benzenesulfinyl)benzonitrile 
• 1158987-01-9 tert-butyl 5'-chloro-2'-{[4-(dimethylamino)phenyl]sulfinyl}biphenyl-4-carboxylate 
• 1309446-18-1 4-((5-chloro-[1,1'-biphenyl]-2-yl)sulfinyl)-N,N-dimethylaniline 
• 1309446-37-4 ethyl 2-(4-chloro-2-((trimethylsilyl)ethynyl)benzyl)acrylate 
• 1309446-20-5 4-((4-chloro-2-((trimethylsilyl)ethynyl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 1309446-19-2 4-((4-chloro-2-(phenylethynyl)phenyl)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.

Methyl sulfinates as electrophiles in friedel-crafts reactions. Synthesis of aryl sulfoxides

The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.

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 an ortho-magnesiation and a subsequent sulfoxide-magnesium exchange

Highly functionalized 1,2,4-trisubstituted arenes can be prepared on large scale by a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metalation directing group, allowing a smooth magnesiation wit

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.