1279130-08-3

Upstream product

• 109-04-6 2-bromo-pyridine 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 

Downstream Products

• 1279130-50-5 bis(2-hydroxy-4-methoxyphenyl) disulfide 
• 1279130-36-7 5-methoxy-2-(2-pyridinylsulfinyl)phenyl acetate 
• 1289560-34-4 2-{4-methoxy-2-[(E)-styryl]phenylsulfinyl}pyridine 
• 1289560-33-3 butyl (E)-3-[5-methoxy-2-(2-pyridylsulfinyl)phenyl]acrylate 
• 1309446-75-0 4-(2-((4-methoxyphenyl)sulfinyl)pyridin-3-yl)benzonitrile 
• 870723-88-9 4-(2-(4-methoxyphenyl)pyridin-3-yl)benzonitrile 
• 1308400-00-1 (E)-methyl 3-(5-methoxy-2-(pyridin-2-ylsulfinyl)phenyl)acrylate 
• 1345470-27-0 2-[(4-methoxy-2-methylphenyl)sulfinyl]pyridine 
• 1345470-29-2 2-[(4-chloro-2-methylphenyl)sulfinyl]pyridine 
• 1345470-21-4 2-[(4'-fluoro-5-methoxybiphenyl-2-yl)sulfinyl]pyridine 

Relevant academic research and scientific papers

Palladium-catalyzed regioselective arylation of arene C-H bond assisted by the removable 2-pyridylsulfinyl group

A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application of the methodology. Georg Thieme Verlag Stuttgart · New York.

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.)

Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions

A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.

2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes

Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.

Palladium(II)-catalyzed direct alkenylation and arylation of arenes: Removable 2-pyridylsulfinyl group assisted C-H bond activation

Palladium-catalyzed C-H activation reactions directed by a removable 2-pyridylsulfinyl group were developed. Aromatic olefination products were formed in good yields on treatment of 2-(phenylsulfinyl)pyridines with alkenes in the presence of a Pd catalyst