5421-44-3

Upstream product

• 106-41-2 4-bromo-phenol 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 100-09-4 4-methoxybenzoic acid 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 701-53-1 p-methoxybenzoyl fluoride 
• 100-07-2 4-methoxy-benzoyl chloride 

Relevant academic research and scientific papers

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.

Pd/C catalyzed phenoxycarbonylation using: N -formylsaccharin as a CO surrogate in propylene carbonate, a sustainable solvent

This work reports the first Pd/C catalyzed phenoxycarbonylation of aryl iodides using N-formylsaccharin as a CO surrogate. Advantageously, the reaction could be carried out in propylene carbonate, an environmentally benign and sustainable polar aprotic solvent under CO surrogacy. Using N-formylsaccharin as a CO surrogate allows the usage of cheaper and readily available phenols as the coupling partner. A range of phenyl esters could be synthesized under mild, co-catalyst free, ligand free and additive free conditions, including multi-substituted novel phenyl esters. The Pd/C catalyst could be recycled up to four times with only a slight loss in activity. The reaction could be scaled up to gram scale synthesis.

Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents

Carbonyl carbon 13C NMR chemical shifts δC(C=O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C 6H4CO2C6H4-p-X (X = NO2, CN, Cl, Br, H, Me, or MeO; Y = NO2, Cl, H, Me, MeO, or NMe2) have been used as a tool to study substituent effects on the carbonyl unit. The goal of the work was to study the cross-interaction between X and Y in that respect. Both the phenyl substituents X and the benzoyl substituents Y have a reverse effect on δC(C=O). Electron-withdrawing substituents cause shielding while electron-donating ones have an opposite influence, with both inductive and resonance effects being significant. The presence of cross-interaction between X and Y could be clearly verified. Electronic effects of the remote aromatic ring substituents systematically modify the sensitivity of the C=O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of δC(C=O) to the substitution of another ring, while electron-donating substituents inversely affect the sensitivity. It is suggested that the results can be explained by substituent-sensitive balance of the contributions of different resonance structures (electron delocalization, Scheme 1).

(Trimethylsilyl)ethoxyacetylene. An Effective Reagent for Mild Dehydrative Condensation of Carboxylic Acids and H-Acidic Materials

(Trimethylsilyl)ethoxyacetylene, a stable and easy to handle dehydrating reagent, is quite effective for the title condensation to prepare ester-, lactone-, lactam-, and peptide-linkages under mild conditions.

A Novel Synthesis of Phenyl Carboxylates

The direct synthesis of phenyl carboxylates from phenols and carboxylic acids is reported.The reactions proceeded easily when triphenylphosphine and carbon tetrachloride were used as dehydrating agents in the presence of a tertiary amine at room temperature, thus giving esters in high yields.

The Synthesis of Phenyl Carboxylates from p-Bromophenol and Carboxylic Acid

The reaction of p-bromophenol with carboxylic acids in the presence of triphenylphosphine and triethylamine proceeded at a high temperature, with the elimination of hydrogen bromide, to give phenyl carboxylates and small amounts of p-bromophenyl carboxylates.