FeCl₃-catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: preparation of selected API impurities

Abstract

There is an ever-increasing demand for impurities required for profiling as regulatory agencies seek information during registration. Herein, we report FeCl3-catalyzed oxidative decarboxylation of aryl-, and heteroaryl acetic acids to...

Synthesis and Characterization of Bimetallic Nanoclusters Stabilized by Chiral and Achiral Polyvinylpyrrolidinones. Catalytic C(sp3)–H Oxidation

“…The 13 C NMR spectrum shows the C6-carbonyl group at δ 207.0 ppm, and the IR spectrum shows it at ν 1695 cm –1 . Compound 48 likely forms from C–H group oxidation at C6 followed by decarboxylative fragmentation to give the ketone function . No oxidation of the alkene function was found, and the oxidation reaction taking place at C6 of 46 , adjacent to the electron-withdrawing group, carboxylic acid, was unusual.…”

“…No oxidation of the alkene function was found, and the oxidation reaction taking place at C6 of 46 , adjacent to the electron-withdrawing group, carboxylic acid, was unusual. Moreover, the C–H group oxidation of cyclic aryl-α-carboxylic acid followed by decarboxylative fragmentation to form the corresponding ketone is a useful process such as ensuring the quality of active pharmaceutical ingredients . Functional group manipulations of 47 and 48 will provide a library of novel derivatives for drug discovery screening .…”

“…Compound 48 likely forms from C−H group oxidation at C6 followed by decarboxylative fragmentation to give the ketone function. 54 No oxidation of the alkene function was found, and the oxidation reaction taking place at C6 of 46, adjacent to the electron-withdrawing group, carboxylic acid, was unusual. Moreover, the C−H group oxidation of cyclic aryl-α-carboxylic acid followed by decarboxylative fragmentation to form the corresponding ketone is a useful process such as ensuring the quality of active pharmaceutical ingredients.…”

“…Moreover, the C−H group oxidation of cyclic aryl-α-carboxylic acid followed by decarboxylative fragmentation to form the corresponding ketone is a useful process such as ensuring the quality of active pharmaceutical ingredients. 54 Functional group manipulations of 47 and 48 will provide a library of novel derivatives for drug discovery screening. 53 To support this oxidative decarbonylation reaction, indane-1-carboxylic acid (49) was treated with 1 mol % Pd/Au-PVP and 1.5 equiv of t-BuOOH in CH 3 CN-H 2 O at 50 °C.…”

Electrochemical Decarboxylative Oxygenation of Carboxylic Acids

“…Carboxylic acids, ubiquitous in biomass sources and industrial feedstocks, are among the most attractive functional groups in organic synthesis. − In this context, carboxylic acids and their activated derivatives readily undergo a diverse range of decarboxylative transformations to form carbon–carbon, carbon–halogen, and other carbon–heteroatom bonds. − In contrast, their decarboxylation and subsequent CO double-bond formation have been rarely explored and only very few papers have been reported to date, typically limited to benzylic carboxylic acids (Scheme A). − Recently, Hosseini-Sarvari demonstrated that carboxylic acids could be converted efficiently to carbonyl-containing compounds including aldehydes and ketones using a Au@ZnO photoredox catalyst (Scheme B) . At almost the same time, MacMillan group disclosed an elegant decarboxylative oxygenation method providing aldehydes, ketones, and amides from readily available carboxylic acids via iridium photoredox catalysis .…”