28122-95-4

Usage

InChI:InChI=1/C11H8OS2/c12-11(10-7-4-8-13-10)14-9-5-2-1-3-6-9/h1-8H

Upstream product

• 3437-95-4 2-Iodothiophene 
• 108-98-5 thiophenol 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 98-03-3 thiophene-2-carbaldehyde 
• 882-33-7 diphenyldisulfane 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 527-72-0 2-thiophenylcarboxylic acid 
• 2361-27-5 2-thienylhydrazide 
• 1449477-04-6 (phenylsulfenyl)zinc bromide 
• 4075-59-6 2-thiopheneglyoxylic acid 
• 1003-09-4 2-bromothiophene 
• 554-14-3 2-Methylthiophene 
• 636-72-6 2-thiophenemethanol 
• 188290-36-0 thiophene 

Downstream Products

• 53451-90-4 phenyl 4-trifluoromethylphenyl sulfide 
• 16718-12-0 2-(Phenylthio)thiophene 
• 791120-35-9 trans-Pt(SPh)[C(O)(2-thienyl)](PPh₃)2 
• 791120-36-0 (PPh3)[(2-thienyl)C(O)]Pt(μ-SPh)2Pt[C(O)(2-thienyl)](PPh3) 
• 610796-53-7 3-bromo-2-phenylthio-1-propene 
• 20876-80-6 phenyl dithio-2-thiophenate 

Relevant academic research and scientific papers

Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters

The reaction of aryl thiophene-2-carbodithioates or thiophene-3-carbodithioates with difluorocarbene generated from BrCF2CO2Li/molecular sieves 4A produced arylsulfanylated 2,2-difluoro-3-thienylthiiranes. In the presence of lithium ion, the thiirane intermediates underwent ring expansion followed by HF elimination, leading to fluorinated thieno[3,2-b]thiophenes or thieno[2,3-b]thiophenes. The reactions of the oxygen analogues, aryl furancarbodithioates, also proceeded to afford the corresponding thieno[3,2-b]furans. Intramolecular fluorine substitution in the produced arylsulfanyl(fluoro)thienofurans allowed for another thiophene ring construction, leading to the synthesis of fused pentacyclic thienothienofurans.

Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters

Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides

An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivativ

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.

Synthesis of Thiol Esters Using PhSZnBr as Sulfenylating Agent: A DFT-Guided Optimization of Reaction Conditions

The use of PhSZnBr as sulfenylating agent in a solvent-free protocol to prepare thiol esters in excellent yields from acyl chlorides is reported. The products were efficiently obtained by grinding the neat reagents for 5 min in a mortar. DFT calculations

Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols

Copper-catalyzed decarboxylative coupling between α-oxocarboxylic acids and diphenyl disulfides or thiophenols is presented, which provided an effective and direct approach for the preparation of useful thioesters through C(sp2)-S bond formatio

Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions

A new polymer supported phosphine free Pd(ii) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the carbonylation of aryl halides into aryl thioesters under mild reaction conditions. Thioesters were obtained in excellent yields from various aryl iodides and thiols in the presence of carbon monoxide and polymer supported palladium catalyst. The effects of solvent, base, reaction time and catalyst amount for the thioester synthesis were reported. This catalyst showed excellent catalytic activity and recyclability. The polymer supported Pd(ii) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.

Iron-catalyzed synthesis of thioesters from thiols and aldehydes in water

The preparation of thioesters through the iron-catalyzed coupling reaction of thiols with aldehydes is described. The reactions were carried out by using tert-butyl hydroperoxide (TBHP) as an oxidant and water as a solvent in most cases. This system is co

Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides

(Chemical Equation Presented) A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along with the weak base, NaOAc, in anisole at 120°C. The choice of catalytic system as well as solvent turned out to be important in order to ensure a high chemoselectivity in the reaction. Both electron-rich and electron-deficient aryl bromides worked well in this reaction. Addition of 1 equiv of sodium iodide to the reaction improved the chemoselectivity with the electron-deficient aryl bromides. The thiol scope included both aryl and alkyl thiols, including 2-mercaptobenzophenones, whereby a thiocarbonylation followed by a subsequent McMurry coupling yielded differently substituted benzothiophenes. It was demonstrated that the methodology could be applied for 13C introduction into the thiophene ring.