24422-71-7

Upstream product

• 4013-34-7 3-phenyl-2-oxabutane 
• 106-54-7 p-Chlorothiophenol 
• 585-71-7 (1-bromoethyl)benzne 
• 51946-00-0 p-ClC₆H₄SGe(CH₃)3 
• 34047-27-3 (p-Cl-phenylthio)trimethylstannane 
• 98-85-1 1-Phenylethanol 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 34713-70-7 2-Phenylpropanal 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 100-41-4 ethylbenzene 
• 2449-49-2 dimethyl(1-phenylethyl)amine 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 

Relevant academic research and scientific papers

Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.

Preparation method of alkyl sulfide

The invention relates to a preparation method of alkyl sulfide. The method comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, a nitrogen ligand, a cocatalyst, an oxidant, a solvent, alkane and thiophenol or mercaptan into a reaction tube, carrying out oxidative dehydrogenation coupling reaction at 80-150 DEG C, ending the reaction after 6-48 hours, evaporating the solvent to dryness, and carrying out column chromatography separation to obtain the alkyl sulfide compound. The method is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.

Eosin-Y-Catalyzed Photoredox C?S Bond Formation: Easy Access to Thioethers

An operationally simple Eosin Y catalyzed sulfenylation of hydrazones has been realized to afford a range of thioethers under visible light. The methodology provides high yields of thioethers under ambient conditions employing readily available and inexpensive starting materials. The reaction has broad substrate scope and is compatible with various functional groups.

Utilizing 2-phenylpropanal as coupling partner for C-S bond formation via sequential thioarylation and decarbonylation process: A novel strategy for the synthesis of aryl alkyl sulfides

In this study, first direct access to aryl alkyl sulfides employing 2-phenylpropanal as coupling partner is reported. Diaryl disulfides react with this aldehyde in the presence of morpholine and produce the corresponding sulfide products in high yields. In another part, disulfides are in situ generated in the reaction mixture from aryl halides/CuI/Cyanodithioformate and coupled with 2-phenylpropanal to access aryl alkyl sulfides.

From the [...] joint into aryl sulfide method (by machine translation)

Aryl thioether in the medical, agricultural, dye industry and the field of functional material has extensive use, human production and life are of far-reaching impact. The present invention firstly to aryl tertiary amine one-step synthesis of aryl thioether compounds, namely in the copper salt catalytic N, N - dimethyl - 1 - (hetero) aryl ethylamine with aryl dithiol to C - S coupling-synthesizing aryl thioether. The method of the invention has high yield, raw materials are easy, simple conditions, environmental protection and the like. (by machine translation)

Copper-Catalyzed Stereospecific C-S Coupling Reaction of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Methyl Triflate

A one-pot protocol for the synthesis of highly enantiopure benzylic thioethers, thioacetates, and sulfones (94-99% ee) via a ligand-free, copper-catalyzed stereospecific C-S coupling reaction of thiols and enantioenriched tertiary benzylic amines via in situ activation by methyl triflate is developed. Various enantioenriched tertiary benzylic amines, including 1-arylalkylamines, 1-tetrahydronaphthylethylamine, heterocyclic amines (e.g., 1-(thiophen-2-yl)ethanamine), and amino acid esters containing a benzylamine moiety, are highly efficient substrates, and their chirality is efficiently transferred to the products (94-99% ee). The absolute configurations of the products are predictable and follow the pattern of SN2-type substitutions; an inversion of the absolute configuration of the tertiary amines occurs during the C-S coupling reaction. Not only are various alkene-, arene-, and heteroarenethiols suitable for this C-S coupling reaction but also potassium thioacetate and sodium phenylsulfinate are as well. A plausible mechanism was proposed on the basis of the experimental results.

Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate

Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S-benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol-%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.

Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols

A metal-free procedure for the synthesis of thioethers is described via the base-promoted reductive coupling of tosylhydrazones with thiols through an insertion of a carbene into the S-H bond.

Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br

An easily accessible and inexpensive room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes the reaction of alkyl halides or acyl halides with thiols without any solvent at room temperature leading to the synthesis of thioethers and thioesters in high yields. This reaction has also been extended for the preparation of dithianes and transthioetherification. The ionic liquid is recovered and recycled for subsequent runs.

Unusual cleavage of ethers by thiophenol on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation: Efficient procedure for the synthesis of thioethers through transthioetherification

Cyclic and open-chain benzylic ethers undergo cleavage by thiophenol on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation to produce the corresponding di- and monothioethers.