17577-20-7

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 100-53-8 phenylmethanethiol 
• 100-44-7 benzyl chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 874-59-9 4-chlorobenzoyl bromide 
• 74-11-3 para-chlorobenzoic acid 
• 201230-82-2 carbon monoxide 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 

Relevant academic research and scientific papers

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Ynamide-Mediated Thioester Synthesis

A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH and indole -NH are compatible with the reaction conditions, rendering their protection unnecessary. Moreover, this method was also amenable to selenoesters.

Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent

Herein, an interesting palladium-catalyzed procedure for the direct carbonylative thiomethylation of aromatic amine derivatives with 4-methylthio-2-butanone is developed. Using 4-methylthio-2-butanone as (methylthio) transfer agent, a variety of corresponding thioesters are obtained with moderate to good yields under base-free condition. In addition, good functional group tolerance can be observed.

Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature

Thioesters play a crucial role in biological systems and serve as important building blocks for organic synthesis. Herein, Eosin Y and TBHP mediated photochemical cross dehydrogenative coupling (PCDC) between feedstock aldehydes and thiols has been descri

An odorless, one-pot synthesis of thioesters from organic halides, thiourea and benzoyl chlorides in water

Thioesterification can be realized via an odorless, one-pot reaction through the in situ generation of S-alkylisothiouronium salts from organic halides and thiourea in aqueous Triton X-100 (TX100) micelles. The protocol is free of foul-smell thiols and or

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

Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A2: Synthesis, spectroscopic and computational studies

4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A2 (PLA2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A 2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA2.

NHC-catalyzed thioesterification of aldehydes by external redox activation

The NHC-catalyzed thioesterification of aromatic or aliphatic aldehydes with a range of thiols was developed in the presence of a stoichiometric amount of an organic oxidant. Among the oxidants examined, phenazine was shown to give the best results in terms of chemical yield and compatibility with thiols.