86763-33-9

Upstream product

• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 26960-77-0 sodium dodecanethiolate 
• 38117-54-3 cyclopentadienyl iron(II) dicarbonyl dimer 
• 112-55-0 1-dodecylthiol 
• 123-11-5 4-methoxy-benzaldehyde 
• 2757-37-1 didodecyl disulfide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 20025-90-5 p-dodecylbenzenethiol 
• 150-76-5 4-methoxy-phenol 
• 1253793-77-9 O-(tert-butyl) S-dodecyl thiocarbonate 
• 66107-29-7 4-methoxyphenyl triflate 

Downstream Products

• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage

A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.

Tunable aryl imidazolium recyclable ionic liquid with dual br?nsted-lewis acid as green catalyst for friedel-crafts acylation and thioesterification

Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.

Microwave-assisted Synthesis of Thioesters from Aldehydes and Thiols in Water

We describe the synthesis of thioesters via copper- or iron-catalyzed coupling of thiols with aldehydes on application of microwave irradiation. In this protocol, a variety of aliphatic and aromatic aldehydes and thiols were used, and the products were ob

Fukuyama reduction and integrated thioesterification/fukuyama reduction of thioesters and acyl chlorides using continuous flow

Fukuyama reduction of thioesters has been achieved using a polymer-supported Pd[0] catalyst (Pd/XAD-4), and continuous flow conditions. The generality of this reaction is good with a range of aldehydes prepared in excellent yields. In addition, an integrated multistep thioesterfication/ Fukuyama reduction has been developed that allows acyl chlorides to be directly converted to the corresponding aldehydes. Integral to this process is the use of polymer-supported amine and isocyanate reagents to achieve thioesterification and scavenge unreacted thiol. In addition, catch-and-release purification has been employed to enable isolation of the aldehyde from silylthioether byproducts without the need for chromatographic purification.

Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions

A DTBP-promoted C-H thiolation of aldehydes with disulfides under metal-free and solvent-free conditions is described. The system shows good functional group tolerance to afford thioesters in moderate to excellent yields. the Partner Organisations 2014.

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

Synthesis of thioesters through copper-catalyzed coupling of aldehydes with thiols in water

Copper-catalyzed C-S bond formation between aldehydes and thiols in the presence of TBHP as an oxidant is described. Functional groups including chloro, trifluoromethyl, bromo, iodo, nitrile, ester and thiophene are all tolerated by the reaction condition

Bis(cyclopentadienyldicarbonyliron) as a convenient carbon monoxide source in palladium-catalyzed carbonylative coupling of aryl iodides with amines, alcohols, and thiols

Bis(cyclopentadienyldicarbonyliron) ([CpFe(CO)2]2) serves as a carbon monoxide source in carbonylative coupling reactions. Treatment of aryl iodides with primary amines in the presence of DBU and [CpFe(CO)2]2 under palladium catalysis provides the corresponding benzamides in good yields. Similar reactions with phenols and thiols provide the corresponding benzoate esters and thioesters, respectively. A catalytic amount of DMAP as an additive promoted the carbonylative coupling reactions with primary alcohol and secondary amine.

Base-induced mechanistic variation in palladium-catalyzed carbonylation of aryl iodides

A mechanism, which is distinct from the traditional one when sodium alkoxide was used instead of tertiary amines, was proposed for the alkoxycarbonylation of aryl iodides. The catalytic cycle was composed of oxidative addition, subsequent ArPdOR formation, CO insertion to Pd-OR, and final reductive elimination of ArPdCOOR. The kinetic simultaneity of the formation of deiodinated side product from the aryl iodide and aldehyde from corresponding alcohol provided strong evidence for the existence of ArPdOR species. The observation of thioether, as the other competitive product in palladium catalyzed thiocarbonylation of aryl iodides and sodium alkylthiolate, also indicate the possibility of metathesis between ArPdl and sodium alkylthiolate. Preliminary kinetic studies revealed that neither oxidative addition nor reductive elimination was rate limiting. DFT calculation displayed preference for CO insertion into Pd-OR bond. The advantage of this novel mechanism had been demonstrated in the facile alkoxycarbonylation and thiocarbonylation. The ethoxycarbonylation of aryl iodides under room temperature and balloon pressure of CO in the presence of EtONa were examined, and good to high yields were obtained; the t-butoxycarbonylation reactions in the presence of t-BuONa were achieved, and the alkylthiocarbonylation (including the t-butylthiocarbonylation) of aryl iodides in the presence of sodium alkylthiolate were also investigated.