119520-56-8

Upstream product

• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 79-06-1 2-propenamide 
• 98-98-6 2-Picolinic acid 
• 1569-69-3 Cyclohexanethiol 
• 109-09-1 2-chloropyridine 
• 109-04-6 2-bromo-pyridine 
• 108-85-0 1-bromocyclohexane 
• 66715-65-9 pyridine-2-sulfonyl chloride 
• 106762-43-0 Piperidin-1-yl pyridin-2-yl sulfone 
• 135763-96-1 cyclohexyl 2-pyridyl sulfoxide 
• 18438-38-5 2-methylsulfanyl-pyridine 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 110-82-7 cyclohexane 
• 1121-30-8 1-hydroxy-2(1H)-pyridinethione 

Downstream Products

• 135763-96-1 cyclohexyl 2-pyridyl sulfoxide 

Relevant academic research and scientific papers

The functionalization of saturated hydrocarbons. Part 34. A study on the mechanism of tempo trapping in GIF-type systems

The photolysis of Barton PTOC esters (radical reaction) in presence of Tempo produces alkyl-Tempo in very good yield. Good results are also obtained with Fe(II)-H2O2 system (pyridine, Picolinic Acid, hydrocarbon). In this case the Fe(II)-Fe(IV) manifold is responsible for the formation of the adduct. Using Fe(III)-H2O2, Tempo adduct is formed at the same rate as the oxidation products. Mechanistic studies suggest the oxidation of Tempo by the Fe(V) to give an oxoammonium salt and an Fe(IV) species.

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

B2cat2-Mediated Reduction of Sulfoxides to Sulfides

An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

Synthesis method of heteroaryl thioether

The invention discloses a synthesis method of heteroaryl thioether. Under the conditions of no catalyst, no solvent, no additive and the like, aryl halide/2-bromopyridine, thiourea and substituted benzyl bromide which are directly taken as raw materials to selectively synthesize asymmetric heteroaryl thioether in one step without using conventional organic sulfides such as mercaptan or thiophenol.The use of organic sulfides with high toxicity and heavy odor, such as mercaptan or thiophenol, is avoided, and the synthesis steps are shortened, so that the synthesis efficiency is improved, the reaction has good selectivity, and the asymmetric thioether can be preferentially obtained.

Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functiona

CATALYTIC C-X-BOND METATHESIS THROUGH ARYLATION

The present invention refers to a process for a catalytic aryl transfer to rearrange the backbone of aromatic C-X bonds.

Metal-free preparation of cycloalkyl aryl sulfides via di-tert-butyl peroxide-promoted oxidative C(sp3)-H bond thiolation of cycloalkanes

A concise thiolation of the C(sp3)-H bond of cycloalkanes with diaryl disulfides in the presence of the oxidant di-tert-butyl peroxide (DTBP) has been developed. This reaction, without using any metal catalyst, tolerates varieties of disulfides and cycloalkanes substrates, giving good to excellent chemical yields, and thus provides a useful approach to cycloalkyl aryl sulfides from unactivated cycloalkanes.

Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions

CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented. The Royal Society of Chemistry 2012.

How solvent modulates hydroxyl radical reactivity in hydrogen atom abstractions

The hydroxyl radical (HO) is a highly reactive oxygen-centered radical whose bimolecular rate constants for reaction with organic compounds (hydrogen atom abstraction) approach the diffusion-controlled limit in aqueous solution. The results reported herein show that hydroxyl radical is considerably less reactive in dipolar, aprotic solvents such as acetonitrile. This diminished reactivity is explained on the basis of a polarized transition state for hydrogen abstraction, in which the oxygen of the hydroxyl radical becomes highly negative and can serve as a hydrogen bond acceptor. Because acetonitrile cannot participate as a hydrogen bond donor, the transition state cannot be stabilized by hydrogen bonding, and the reaction rate is lower; the opposite is true when water is the solvent. This hypothesis explains hydroxyl radical reactivity both in solution and in the gas phase and may be the basis for a containment strategy used by Nature when hydroxyl radical is produced endogenously.