18241-65-1

Upstream product

• 10557-67-2 N-nitroso-p-methyl-acetanilide 
• 104411-45-2 phenyl phenyldithioacetate 
• 106-45-6 para-thiocresol 
• 103-80-0 phenylacetyl chloride 
• 18245-74-4 S-phenyl 2-phenylethanethioate 
• 106871-53-8 2-(p-tolylthio)-2-oxoacetic acid 
• 100-44-7 benzyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 13939-06-5 molybdenum hexacarbonyl 
• 14040-11-0 tungsten hexacarbonyl 
• 103-82-2 phenylacetic acid 
• 930-69-8 sodium thiophenolate 
• 38042-52-3 2-chloro-2-(phenylsulfinyl)-1-phenyl-1-ethanone 

Downstream Products

• 378791-48-1 p-methylphenyl phenyldithioacetate 
• 5023-60-9 1-benzylsulfanyl-4-methyl-benzene 

Relevant academic research and scientific papers

Method for preparing thioester compounds through carbonylation

The invention discloses a method for preparing thioester compounds through carbonylation, wherein the method comprises the following steps: adding palladium acetate, 4,5-bis(diphenylphosphine)-9,9-dimethyl xanthene, tungsten carbonyl, triethylamine, water, a benzyl chloride compound and sulfonyl chloride into an organic solvent, collecting, reacting at the temperature of 100 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the thioester compounds. The preparation method is simple to operate, the initial raw materials of the reaction are cheap and easy to obtain, sulfonyl chloride is used as a sulfur source, and a thiol compound with unpleasant smell can be prevented from being used. The substrate is high in designability, the tolerance range of functional groups of the substrate is wide, and the reaction efficiency is high. Tungsten carbonyl can be used as a carbonyl source and a reducing agent, and an additional reducing agent is not needed. Various thioester compounds can be synthesized according to actual requirements, so that the practicability of the method is widened while the operation is convenient.

Palladium-Catalyzed Thiocarbonylation of Benzyl Chlorides with Sulfonyl Chlorides for the Synthesis of Arylacetyl Thioesters

A convenient procedure for the synthesis of thioesters has been developed via a palladium-catalyzed thiocarbonylation of benzyl chlorides with sulfonyl chlorides. Various arylacetyl thioesters were produced in good yields by using sulfonyl chlorides as an odorless sulfur source. Furthermore, W(CO)6 exhibited dual roles as both a solid CO surrogate and reductant here. (Figure presented.).

A Mild Method for Access to α-Substituted Dithiomalonates through C-Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides

An efficient method for targeting a variety of symmetrical and asymmetrical α-substituted dithiomalonates (DTMs) is described, utilizing 1H-imidazole-1-carbothioates as reactive acylating agents and MgBr2?OEt2/DBU or LiHMDS for soft or hard enolization conditions of thioesters, respectively. The utility of this methodology was demonstrated through the synthesis of the pyridopyrimidine mesoionic insecticides: triflumezopyrim and dicloromezotiaz. (Figure presented.).

Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation

An efficient and convenient strategy for the preparation of diaryl sulfides via a Fe-promoted direct sulfuracylation of 2-naphthylamine using thioesters as bifunctional reagents is described. This synthetic strategy features high chemoselectivity, good substrate scope and functional group tolerance. (Figure presented.).

Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation

Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.

Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis

Direct thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.

Kinetics and mechanism of the aminolysis of aryl phenyldithioacetates in acetonitrile

The aminolysis reactions of Z-aryl phenyldithioacetates (C6H5CH2C(=S)SC6H4Z) with benzylamines (XC6H4CH2NH2) are investigated in acetonitrile at -25.0 °C. T

Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides

A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at -78°C to give alkynolate via alkylidene carbenoid. This intermediate was treated with alcohols, thioles, 5% aqueous NaOH, and amine hydrochlorides to afford one-carbon homologated esters, thioesters, carboxylic acids and amides, respectively, in good to excellent yields.