75915-29-6

Upstream product

• 98-88-4 benzoyl chloride 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 582-61-6 benzoyl azide 
• 65-85-0 benzoic acid 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 74542-54-4 N,N-phenyl-p-toluenesulfonylbenzamide 
• 619-44-3 methyl 4-iodobenzoate 
• 6018-89-9 nickel(II) acetate tetrahydrate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 99-96-7 4-hydroxy-benzoic acid 
• 28547-23-1 4-(benzoyloxy)benzoic acid 

Downstream Products

• 28547-23-1 4-(benzoyloxy)benzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 106782-33-6 3-benzoyl-4-hydroxybenzoic acid 
• 24197-73-7 S-4-methoxyphenyl benzothioate 
• 443296-85-3 4-(benzoyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide 
• 84159-96-6 4-(benzoyloxy)benzoic acid hydrazide 

Relevant academic research and scientific papers

7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Self-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the C aryl-O acylcross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced C aryl-O acylbond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

Esterification of Carboxylic Acids with Aryl Halides via the Merger of Paired Electrolysis and Nickel Catalysis

Electrochemistry has been successfully applied in metal catalysis to avoid the usage of chemical redox agents. This strategy proved to be a powerful approach to construct carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. However, most of the developed methods are based on either anodic oxidation or cathodic reduction, in which a sacrificial reaction occurs at the counter electrode. Paired electrolysis merging with metal catalysis is underdeveloped, wherein both anodic and cathodic processes are taking place simultaneously. Herein, we demonstrated that by using esterification of carboxylic acids with aryl halides via paired electrolysis using nickel as the catalyst the respective aryl esters were obtained in good to excellent yields at room temperature in an undivided electrochemical cell.

Conversion of esters to thioesters under mild conditions

We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.

PEROVSKITES FOR PHOTOCATALYTIC ORGANIC SYNTHESIS

Nature is capable of storing solar energy in chemical bonds via photosynthesis through a series of C—C, C—O and C—N bond-forming reactions starting from CO2 and light. Direct capture of solar energy for organic synthesis is a promising approach

General Paradigm in Photoredox Nickel-Catalyzed Cross-Coupling Allows for Light-Free Access to Reactivity

Self-sustained NiI/III cycles are established as a potentially general paradigm in photoredox Ni-catalyzed carbon–heteroatom cross-coupling reactions through a strategy that allows us to recapitulate photoredox-like reactivity in the absence of light across a wide range of substrates in the amination, etherification, and esterification of aryl bromides, the latter of which has remained, hitherto, elusive under thermal Ni catalysis. Moreover, the accessibility of esterification in the absence of light is especially notable because previous mechanistic studies on this transformation under photoredox conditions have unanimously invoked energy-transfer-mediated pathways.

Dual aminoquinolate diarylboron and nickel catalysed metallaphotoredox platform for carbon-oxygen bond construction

Herein, aminoquinolate diarylboron complexes are utilized as photocatalysts in dual Ni/photoredox catalyzed carbon-oxygen construction reactions. Via this unified metallaphotoredox platform, diverse (hetero)aryl halides can be conveniently coupled with acids, alcohols and water. This method features operational simplicity, broad substrate scope and good compatibility with functional groups. This journal is

Visible light-mediated transition metal-free esterification of amides with boronic acids

A novel strategy for visible light-mediated esterification of amides with boronic acids in air has been described. This method is characterized by mild reaction conditions and low cost owing to no need of any catalyst, which implies high potential utility in late-stage functionalization of amide drugs and materials.

Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).

Semi-heterogeneous Dual Nickel/Photocatalysis using Carbon Nitrides: Esterification of Carboxylic Acids with Aryl Halides

Cross-coupling reactions mediated by dual nickel/photocatalysis are synthetically attractive but rely mainly on expensive, non-recyclable noble-metal complexes as photocatalysts. Heterogeneous semiconductors, which are commonly used for artificial photosynthesis and wastewater treatment, are a sustainable alternative. Graphitic carbon nitrides, a class of metal-free polymers that can be easily prepared from bulk chemicals, are heterogeneous semiconductors with high potential for photocatalytic organic transformations. Here, we demonstrate that graphitic carbon nitrides in combination with nickel catalysis can induce selective C?O cross-couplings of carboxylic acids with aryl halides, yielding the respective aryl esters in excellent yield and selectivity. The heterogeneous organic photocatalyst exhibits a broad substrate scope, is able to harvest green light, and can be recycled multiple times. In situ FTIR was used to track the reaction progress to study this transformation at different irradiation wavelengths and reaction scales.