106920-23-4

Upstream product

• 2637-34-5 2-Sulfanylpyridine 
• 625-99-0 3-iodochlorobenzene 
• 29878-59-9 thiolate of 2-mercaptopyridine 
• 109-04-6 2-bromo-pyridine 
• 2037-31-2 3-chlorophenylthiol 
• 109-09-1 2-chloropyridine 

Downstream Products

• 110-86-1 pyridine 
• 3111-54-4 2-phenylsulfanylpyridine 
• 1289560-80-0 2-[(3-chlorophenyl)sulfinyl]pyridine 
• 1289560-39-9 butyl (E)-3-[4-chloro-2-(2-pyridylsulfinyl)phenyl]acrylate 
• 3111-54-4 2-Phenylsulfanyl-pyridine 

Relevant academic research and scientific papers

2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C-H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant

Pd(II)-catalyzed C-H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulf

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.

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.

Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives

A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and>99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.

Monosubstitution versus Disubstitution in the SRN1 Reaction of Dihalobenzenes with Sulfanions. The Role of the Monosubstitution Product and of Its Anion Radical

The competition between mono- and disubstitution of dihalobenzenes by a series of aromatic sulfanions, via the SRN1 reaction, is shown to involve two radical chains.The first one, recognized in earliest works, involves one branching point at the level of the monosubstituted product anion radical.Reoxidation of the latter via electron transfer to the parent dihalide affords the monosubstituted product.Conversely, the route to the disubstituted product is opened when cleavage of the carbon-halogen bond in the monosubstituted product anion radical occurs before the electron transfer takes place; the disubstitution product is then obtained in its reduced (anion radical) form.Reoxidation of the latter, to afford the neutral disubstituted product, may involve competitively the parent dihalide or the neutral monosubstituted product, depending on the electron affinity of the arylthio moiety.In the first case the electron transfer propagates the first chain; in the second a new chain leading to the disubstitution is activated.The role of the two imbricated chains, under photochemical conditions, and thus that of the monosubstitution product is discussed quantitatively on the basis of the pertinent rate constants determined by cyclic voltammetry.