Synthesis of Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes

Synthesis ◽  
2021 ◽  
Author(s):  
Tetsuya Satoh ◽  
Yasuhito Inai ◽  
Yoshinosuke Usuki
Keyword(s):  
Carboxylic Acids ◽  
Catalyst System ◽  
Benzoic Acids ◽  
Naphthalene Derivatives ◽  
Aromatic Carboxylic Acids ◽  
Internal Alkynes ◽  
Decarboxylative Coupling ◽  
Substituted Benzoic Acids ◽  
Cyclic Compounds

AbstractThe decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)]2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted naphthalene derivatives. The catalyst system is applicable to constructing anthracene and benzo­[c]thiophene frameworks through reactions of naphthoic and thiophene-2-carboxylic acids, respectively.

Oxidative C-H Acyloxylation of Acetone with Carboxylic Acids under Iodine Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen
Keyword(s):  
Carboxylic Acids ◽  
Sodium Chlorite ◽  
Benzoic Acids ◽  
Aromatic Carboxylic Acids ◽  
Substituted Benzoic Acids

Iodine catalyzed oxidative C(sp3)-H acyloxylation of acetone with carboxylic acids has been developed. The method employs an iodide as catalyst and sodium chlorite as oxidant. Substituted benzoic acids, naphthoic acids and hetero-aromatic carboxylic acids can be used, and 2-oxopropyl carboxylates are obtained with good to excellent yields.

An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides

2016 ◽  
Vol 14 (1) ◽  
pp. 246-250 ◽  
Author(s):  
Bing Mu ◽  
Yusheng Wu ◽  
Jingya Li ◽  
Dapeng Zou ◽  
Junbiao Chang ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Aromatic Carboxylic Acids ◽  
Aryl Chlorides ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

An efficient and facile protocol for the synthesis of 3-aryl-imidazo[1,2-a]pyridines was investigated via palladium-catalyzed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids.

Electrostatic effects on ionization equilibria: Solvent dependence

1984 ◽  
Vol 49 (1) ◽  
pp. 179-189 ◽  
Author(s):  
Karel Kalfus ◽  
Zdeněk Friedl ◽  
Otto Exner
Keyword(s):  
Gas Phase ◽  
Carboxylic Acids ◽  
Dissociation Constants ◽  
Aprotic Solvents ◽  
Benzoic Acids ◽  
Cavity Model ◽  
Electrostatic Effects ◽  
Solvent Dependence ◽  
Ionization Equilibria ◽  
Substituted Benzoic Acids

Apparent dissociation constants of 3-substituted bicyclo[2,2,2]-octane-1-carboxylic acids I-III and of several substituted benzoic acids were measured in four pure solvents. The results - together with numerous literature data concerning dissociation in other solvents and in the gas phase - were compared with the prediction of the electrostatic theory. The theory fails to reproduce the essential features of the solvent dependence as it predicts generally too small effects and does not differentiate between protic and aprotic solvents. The mentioned goal cannot be achieved by any more sophisticated cavity model or by any other theory as far as it characterizes the solvent only through its bulk permittivity.

Synthesis of perbromobenzoic acids and perbromobenzenes from aromatic carboxylic acids by permercuration and bromodemercuration

1977 ◽  
Vol 30 (2) ◽  
pp. 293 ◽  
Author(s):  
GB Deacon ◽  
GJ Farquharson
Keyword(s):  
Thermal Decomposition ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Benzoic Acids ◽  
Similar Treatment ◽  
Aromatic Carboxylic Acids ◽  
Effect Of Substituents

Permercuration of the benzoic acids XC6H4CO2H (X = o-Me, F, Cl, or Br; m- Me, F, Cl, Br, CF3, NO2 or OMe; or p-Me, F, Cl, Br, CF3 or NO2) and 2,6- X2C6H3CO2H (X = Me, Cl, or Br) with molten mercuric trifluoroacetate at c. 180-245° followed by bromodemercuration gave the corresponding perbromobenzoic acids XC6Br4CO2H or 2,6-X2C6Br3CO2H, together with the corresponding perbromobenzenes C6Br5X or m-X2C6Br4 which were formed owing to decarboxylation under permercuration conditions. Similar treatment of the acids XC6H4CO2H (X = o-NO2, CF3, or OMe; or p-OMe) and 2,6-F2C6H3CO2H gave only the appropriate perbromobenzenes. Possible mechanisms for permercuration induced decarboxylation are proposed on the basis of the effect of substituents on yields of perbromobenzoic acids and perbromobenzenes. Decarboxylation occurs more widely under permercuration conditions than on pyrolysis of mercuric carboxylates. Regiospecific mercuration meta to the carboxyl group and not decarboxylation occurred on thermal decomposition of mercuric p-methoxybenzoate.

Rhodium-catalyzed regiospecific C–H ortho-phenylation of benzoic acids with Cu/air as an oxidant

2017 ◽  
Vol 4 (3) ◽  
pp. 417-420 ◽  
Author(s):  
Shiguang Li ◽  
Guo-Jun Deng ◽  
Feifei Yin ◽  
Chao-Jun Li ◽  
Hang Gong
Keyword(s):  
Carboxylic Acids ◽  
Synthetic Approach ◽  
Benzoic Acids ◽  
Aromatic Carboxylic Acids

An efficient and practical synthetic approach for the regiospecific C–H ortho-phenylation of aromatic carboxylic acids in the absence of silver.

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