17577-22-9

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 100-53-8 phenylmethanethiol 
• 150-60-7 dibenzyl disulphide 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-39-0 benzyl bromide 
• 794-94-5 p-Methoxybenzoic anhydride 
• 58618-94-3 benzoic p-methoxybenzoic anhydride 
• 100-09-4 4-methoxybenzoic acid 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 201230-82-2 carbon monoxide 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 701-53-1 p-methoxybenzoyl fluoride 
• 104-47-2 p-methoxybenzylnitrile 

Relevant academic research and scientific papers

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.

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides

An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivativ

Rapid synthesis of acyl fluorides from carboxylic acids with Cu(O2CCF2SO2F)2

Acyl fluorides have moderate electrophilicity and a very good balance between stability and reactivity. Utilization of acyl fluorides as versatile building blocks in transition-metal catalysis attracts fast-growing and great attention recently. Development of rapid and operationally simple synthetic methods for acyl fluorides has always been desirable. We report herein a rapid, simple and efficient acyl fluoride synthesis from carboxylic acids with Cu(O2CCF2SO2F)2 as a deoxofluorination reagent. Notably, Cu(O2CCF2SO2F)2 was readily prepared in large scale from inexpensive starting material, and previously used as a good trifluoromethylating reagent.

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.

A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp3)-H-Oxidation of Benzylic Nitriles

A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru-catalyzed selective C?H-oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C?H-oxidation-Tischenko-rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.

One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions

In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.

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

Microwave-assisted direct thioesterification of carboxylic acids

A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.

Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters

A novel, efficient, metal-, base- and acid-free straightforward protocol has been developed for the construction of useful thioesters. The immense catalytic potential of HFIP for promoting the thiocarbonylation of acyl halides and thiols is disclosed. HFIP was recovered with ease and reused for further reactions without any loss of reactivity. Both aryl and alkyl thiols bearing electron-donating and electron-withdrawing groups as well as aryl- and alkyl acyl halides worked well in this reaction. Inexpensive precursors, short reaction time, obviating workup, high atom economy, and gram-scale preparation are the significant features of the developed eco-friendly route for S-carbonylation of thiols.