133535-77-0

Upstream product

• 100-53-8 phenylmethanethiol 
• 65439-56-7 3-phenyl-1-(2-thioxothiazolidin-3-yl)propan-1-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 150-60-7 dibenzyl disulphide 
• 645-45-4 hydrocinnamic acid chloride 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 2021-28-5 ethyl dihydrocinnamate 
• 100-39-0 benzyl bromide 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 97723-86-9 3-phenylthiopropionic acid S-4-chlorophenyl ester 
• 23522-73-8 3-phenylpropionic acid 4-chlorophenyl ester 
• 179386-76-6 1-(1H-benzotriazol-1-yl)-3-phenylpropan-1-one 

Relevant academic research and scientific papers

Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light

A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.

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

C-C Bond Cleavage of Unactivated 2-Acylimidazoles

2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

Palladium-Catalyzed Enantioselective Thiocarbonylation of Styrenes

A highly enantioselective thiocarbonylation of styrenes with CO and thiols has been achieved by Pd catalysis, providing highly enantioenriched thioesters in good to excellent yields. Key to the successful execution of this reaction is the use of a chiral sulfoxide-(P-dialkyl)-phosphine (SOP) ligands. This thiocarbonylation proceeds smoothly under mild reaction conditions (1 atm CO and 0 °C) and displays broad substrate scope. Also demonstrated is that this transformation can be conducted using surrogates of CO, greatly increasing the safety aspects of running the reaction. The generality and utility of the method is manifested by its application to the synthetic transformations of thioester products and the direct acylation of cysteine-containing dipeptides. A primary mechanism was investigated and a plausible catalytic cycle was proposed.

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.

Syntheses and reactivities of non-symmetrical "active ester" bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group

We have newly synthesized the non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazole group (i.e., 9, 15, and 16) on the basis of the reactivity study of the "active ester" model compounds, 11-14, toward the various nucleophiles and examined their reaction selectivity towards the same nucleophiles. Then, we applied for the modification of cholesterol at the more reactive site of the bi-dentate linkers to give 3β-cholesteryl 4-(phthalimidoyloxycarbonyl)butyrate (39), and the subsequent reaction of 39 with several amines, such as benzylamine, 4-chlorobenzylamine, 2-phenylethylamine, l-phenylalanine methyl ester, or diphenylalanine benzyl ester as a protein model of the cholesterol antigen.

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.

First synthesis of non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazol group

For the purpose of modification of a variety of derivatives, including biologically important compounds, such as sugar derivatives and proteins etc., we have first synthesized several non-symmetrical bi-dentate cross-linking reagents, namely 3-(phthalimidoyloxycarbonyl)butyric acid chloride (1), 4-(2-benzothiazolyloxycarbonyl)butyric-N-hydroxyphthalimide ester (4) and 4-(1-benzotriazoleoxa)butyric-N-hydroxyphthalimide ester (5).

A novel approach for the direct conversion of alkylsulfonyl derivatives into alkylcarbonyl derivatives via tin-free radical carbonylation

A novel radical approach for the direct conversion of RSO2X into RCOX in a single step is devised; the present approach is very simple, highly efficient, and minimizes formation of by-product. The Royal Society of Chemistry.

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.