Decarboxylative amination of benzoic acids bearing electron-donating substituents and nonactivated amines was written by Wang, Feilong;Han, Ying;Yu, Le;Zhu, Dianhu. And the article was included in Organic Chemistry Frontiers in 2022.Electric Literature of C12H12N2O The following contents are mentioned in the article:
A highly desirable and straightforward decarboxylative amination of readily available benzoic acids, with the long-inaccessible extension of decarboxylative amination to normally poorly reactive electron-rich benzoic acids and non-activated amines for synthesis of anilines RNR1R2 [R = 2-MeOC6H4, 2,6-di-MeC6H3, 2-methoxy-3-pyridyl, etc.; R1 = H, Me; R2 = Ph, Bn, 2-naphthyl, etc.; R1R2 = CH2CH2OCH2CH2] in moderate to high yields with excellent functional-group tolerance was reported. This aniline synthesis was applicable to a wide range of aryl/alkyl/heterocyclic amines under oxidant-free conditions, preventing adverse reactions compared to traditional methods. It also provided decarboxylative C-N modifications of complex bioactive nitrogen-bearing mols. to highlight the synthetic utility of this protocol. The theor. calculation had supported that this decarboxylative amination might proceeded via a concerted decarboxylation-iodination-type process to afford aryl iodine intermediates, which promoted a palladium-catalyzed C-N cross-coupling pathway under mild conditions. Notably, this efficient reaction featured a fine choice of the same base/solvent system to successfully achieve two independent reactions in a one-pot continuous operation process. This strategy provided a method for previously inaccessible decarboxylative amination of benzoic acids bearing electron-donating substituents, as a new alternative to the existing decarboxylative oxidative couplings. This study involved multiple reactions and reactants, such as N-(4-Methoxyphenyl)pyridin-3-amine (cas: 562085-85-2Electric Literature of C12H12N2O).
N-(4-Methoxyphenyl)pyridin-3-amine (cas: 562085-85-2) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Electric Literature of C12H12N2O
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem