13910-16-2

Upstream product

• 111-83-1 1-bromo-octane 
• 3111-52-2 potassium thiophenolate 
• 151-50-8 potassium cyanide 
• 111-66-0 oct-1-ene 
• 108-98-5 thiophenol 
• 75-15-0 carbon disulfide 
• 111-87-5 octanol 
• 111-85-3 n-chlorooctane 
• 121033-26-9 2-(thiophenoxy)nonanal 
• 628-71-7 1-Heptyne 
• 1070-00-4 trioctylaluminum 
• 931-59-9 benzenesulfenyl chloride 
• 30506-39-9 phenyl 1-octyl sulfoxide 
• 66660-08-0 ((3-iodopropyl)thio)benzene 

Downstream Products

• 34009-05-7 (octane-1-sulfonyl)-benzene 
• 16727-37-0 1,1-Diphenylnonan-1-ol 
• 195884-38-9 1-(homoallyloxy)-1-(phenylthio)octane 
• 65094-83-9 S-(n-octyl)-S-phenyl-N-(p-tolylsulfonyl)sulfimide 
• 65094-83-9 S-(n-octyl)-S-phenyl-N-(p-tolylsulfonyl)sulfimide 
• 96456-69-8 2-[3-(4-octylsulfanyl-phenyl)-3-oxo-propyl]-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one 
• 463-11-6 1-Fluoro-octane 
• 65842-42-4 S-phenyl octanethioate 
• 124-07-2 Octanoic acid 
• 111-11-5 methyl octanate 
• 93810-44-7 3-chloro-1-(4-octylsulfanyl-phenyl)-propan-1-one 
• 73242-04-3 4-Octylmercapto-benzophenon 
• 23602-00-8 N-(octan-2-yl)acetamide 
• 30506-39-9 phenyl 1-octyl sulfoxide 

Relevant academic research and scientific papers

Sulfonium Salts as Liquid-Liquid Phase-Transfer Catalysts

Lauryldimethylsulfonium and tri(n-butyl)sulfonium salts serve as highly efficient catalysts for two-phase reactions.

Triphenylsulfonium Salts as Effective Phase Transfer Catalysts under Alkaline Conditions

Triphenylsulfonium salts work as effective phase transfer catalysts for nucleophilic substitution reactions on alkyl halides (e.g. 1) and addition reaction of dichlorocarbene to cyclohexene (8) under strongly alkaline conditions.

Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution

Electrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C-H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

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.

Facile Thiol–Ene Click Protocol Using Benzil as Sensitizer and White LED as Light Source

The thiol–ene reaction leading to a series of thioether derivatives by simple metal and oxidant free visible light promoted photosensitized protocol, following anti-Markonikov hydrothiolation of unactivated aryl and alkyl olefins at room temperature is demonstrated. Benzil served as a green photosensitizer in this reaction and white LED lights as a light source. This radical based thiol–ene reaction is operationally simple and tolerates a wide variety of functional groups present in olefins.

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.

Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.

The energy-transfer-enabled biocompatible disulfide–ene reaction

Sulfur-containing molecules participate in many essential biological processes. Of utmost importance is the methylthioether moiety, present in the proteinogenic amino acid methionine and installed in tRNA by radical-S-adenosylmethionine methylthiotransferases. Although the thiol–ene reaction for carbon–sulfur bond formation has found widespread applications in materials or medicinal science, a biocompatible chemo- and regioselective hydrothiolation of unactivated alkenes and alkynes remains elusive. Here, we describe the design of a general chemoselective anti-Markovnikov hydroalkyl/aryl thiolation of alkenes and alkynes—also allowing the biologically important hydromethylthiolation—by triplet–triplet energy transfer activation of disulfides. This fast disulfide–ene reaction shows extraordinary functional group tolerance and biocompatibility. Transient absorption spectroscopy was used to study the sensitization process in detail. The hereby gained mechanistic insights were successfully employed for optimization of the catalytic system. This photosensitized transformation should stimulate bioimaging applications and carbon–sulfur bond-forming late-stage functionalization chemistry, especially in the context of metabolic labelling.

Metal–organic framework MOF-199-catalyzed direct and one-pot synthesis of thiols, sulfides and disulfides from aryl halides in wet polyethylene glycols (PEG 400)

A highly porous metal–organic frame work Cu3 BTC2 (copper(II)-benzene-1,3,5-tricarboxylate) that is known as MOF-199 was synthesized from the reaction of 1,3,5-benzenetricarboxylic acid and Cu(OAc)2·H2O by a solvothermal method and characterized by several techniques including FT-IR, XRD, EDX and scanning electron microscopy. The MOF-199 used as an efficient catalyst for one-pot synthesis of thiols by domino reactions of aryl halides and thiourea, and subsequently conversion to aryl alkyl sulfides and diaryl disulfides in polyethylene glycols (PEGs). A variety of aryl alkyl sulfides can be obtained in good to excellent yields in a relatively short reaction time and in the presence of the trace amount of catalyst. Also, the catalyst can be separated from the reaction mixture by decanting, and be reused without significant degradation in catalytic activity.