59985-46-5

Upstream product

• 111-83-1 1-bromo-octane 
• 106-54-7 p-Chlorothiophenol 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 111-66-0 oct-1-ene 
• 5138-90-9 sodium 4-chlorobenzenesulfonate 
• 106-39-8 bromochlorobenzene 
• 111-88-6 Octanethiol 

Downstream Products

• 1027507-83-0 1-[1-(4-Chloro-phenylsulfanyl)-octyloxy]-2,4-diheptyl-benzene 
• 1027263-15-5 C₂₁H₂₇ClOS 
• 144265-66-7 1-(1-Chloro-octyloxy)-2,4-diheptyl-benzene 
• 144265-63-4 1-(1-Chloro-octyloxy)-2-methyl-benzene 
• 144265-60-1 1-Chloro-4-(1-chloro-octylsulfanyl)-benzene 
• 105891-21-2 1-Chloro-4-(octane-1-sulfonyl)-benzene 

Relevant academic research and scientific papers

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.

Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water

A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.

A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides

The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.

Synthesis of α-chloroalkyl ethers from phenols

α-Chloroalkyl aryl ethers has been obtained in good yields from phenols and aryl α-chloroalkyl sulfides.