53573-33-4

Upstream product

• 108-98-5 thiophenol 
• 501-52-0 3-Phenylpropionic acid 
• 4551-15-9 phenylthiotrimethylsilane 
• 21273-15-4 trimethylsilyl ester of hydrocinnamic acid 
• 111171-84-7 4-phenyl-1,1,1-tris(phenylthio)butane 
• 104-53-0 3-phenyl-propionaldehyde 
• 882-33-7 diphenyldisulfane 
• 23522-73-8 3-phenylpropionic acid 4-chlorophenyl ester 
• 97723-86-9 3-phenylthiopropionic acid S-4-chlorophenyl ester 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 4119-41-9 1-iodo-3-phenylpropan 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 66132-97-6 2-trimethylsilyl-4-phenyl-1-oxa-1,3-butadiene 
• 63578-13-2 1-(trimethylsilyl)-3-phenyl-1-(trimethylsiloxy)-1-propene 
• 66132-89-6 trimethyl<2-(phenylthio)-3-phenylpropanoyl>silane 
• 66132-93-2 1-trimethylsilyl-3-phenyl-2-phenylsulphinylpropan-1-one 
• 144914-78-3 1-(trimethylsilyl)-3-phenylpentan-1,4-dione 
• 1052108-49-2 C₂₁H₂₄O₂S 
• 68117-68-0 3-phenyl-1-phenylsulphenyl-1-trimethylsiloxypropene 

Relevant academic research and scientific papers

Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.

Manganese(iii)-promoted thiocarbonylation of alkylborates with disulfides: synthesis of aliphatic thioesters

A Mn(iii)-promoted thiocarbonylation procedure toward the synthesis of thioesters has been developed. By employing easily available disulfides and potassium alkyltrifluoroborates as the starting materials, and cheap and non-toxic Mn(OAc)3·2H2O as the promotor, a broad range of thioesters were synthesized in good to excellent yieldsviaradical intermediates.

Palladium-catalyzed thiocarbonylation of alkenes toward linear thioesters

Thiocarbonylation of alkenes offers an ideal procedure for the synthesis of thioesters. However, thiocarbonylation of alkenes, especially styrenes, to produce valuable linear thioesters has remained a challenge. In this Letter, a general palladium-catalyz

ANTIBACTERIAL BETA-LACTONES, AND METHODS OF IDENTIFICATION, MANUFACTURE AND USE

The invention encompasses antibacterial beta-lactones, methods of making, pharmaceutical preparations thereof, and methods of utilization of such compounds for the treatment of bacterial infections.

Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by Mechanochemistry

Acylation reactions are ubiquitous in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products resulting from the acylation of amines and other nucleophiles. Thus, utilisation of N,N′-carbonyldiimidazole (CDI) allows efficient coupling between carboxylic acids and various nucleophiles under solvent-free mechanical agitation, and water-assisted grinding enables both the purification and isolation of pure products. Critical parameters such as the physical state and water solubility of the products, milling material, type of agitation (vibratory or planetary) as well as contamination from wear are analysed and discussed. In addition, original organic-solvent-free conditions are proposed to overcome the limitations of this approach. The calculations of various green metrics are included, highlighting the particularly low environmental impact of this strategy.

Tetraethylammonium bromide-catalyzed oxidative thioesterification of aldehydes and alcohols

A metal-free, tetraethylammonium bromide-catalyzed oxidative coupling of aldehydes or alcohols with thiophenols or disulfides has been developed. This protocol affords an efficient and inexpensive approach to the synthesis of a wide range of thioesters in high yields. Copyright

Fe-catalyzed thioesterification of carboxylic esters

Second nature: Starting from shelf-stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical-ligation-type peptide formation, which suggests that the thiol may act as a co-catalyst for future 1,2-additions of pronucleophiles to carboxylic esters.

Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively

We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.

A convenient method for the synthesis of carboxamides and thioesters by using tetrakis(2-methylimidazol-1-yl)silane

Tetrakis(2-methylimidazol-1-yl)silane [Si(2-Me-Im)4], a new dehydrating reagent having silicon-imidazole linkage, reacted readily with carboxylic acids at room temperature to form the corresponding 1-acyl-2-methylimidazole intermediates, which smoothly underwent subsequent condensation with nucleophiles such as amines or thiols to afford the corresponding carboxamides or thioesters in good to excellent yields, respectively.

Efficient synthesis of thioesters and amides from aldehydes by using an intermolecular radical reaction in water

The combination of the water-soluble radical initiator, 2,2′-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044) and the surfactant, cetyltrimethyl-ammonium bromide (CTAB), was found to be the most suitable condition for the effective and direct synthesis of useful active thioesters (pentafluorophenyl thioesters) in water. In addition, the direct amidation of aldehydes was achieved by the addition of the amines to the thioesterification reaction mixture in water.