Copper-catalyzed efficient access to 2,4,6-triphenyl pyridinesviaoxidative decarboxylative coupling of aryl acetic acids with oxime acetates

Abstract

An efficient and concise approach for the synthesis of 2,4,6-triphenyl pyridines has been developed through copper-catalyzed oxidative decarboxylation coupling of C(sp3) aryl acetic acids with oxime acetates in DMF at...

Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation

“…Based on the above results and previous studies, 18 − 20 the plausible mechanism of the present reaction is illustrated in Scheme 5 . In the first step, arylacetic acid gives araldehyde ( A ) via oxidative decarboxylation in the presence of a copper catalyst under an oxygen atmosphere.…”

“…In our previous work, we identified that arylacetic acids can be converted into aldehydes via oxidative decarboxylation in the presence of a copper catalyst under an oxygen atmosphere ( Scheme 4 , eq 2). 18 As shown in eq 3, when we performed the reaction of benzaldehyde with aryl hydrazide under standard conditions, the desirable product 3 was obtained in a 92% yield. It strongly revealed that benzaldehyde is formed as an intermediate in the reaction.…”

“…Moreover, arylacetic acids are cheap, commercially available, nontoxic, and easy to handle, thus making it advantageous to be used as an ideal starting material. Recently, our group reported the synthesis of 2,4,6 triphenyl pyridines using oxime acetates and arylacetic acids via oxidative decarboxylative cyclization . As a continuous study on this field, we visualized that 2,5-disubstituted 1,3,4-oxadiazoles could be synthesized from aryl hydrazides and arylacetic acids via dual oxidation using oxygen as the sole terminal oxidant.…”

“…Recently, our group reported the synthesis of 2,4,6 triphenyl pyridines using oxime acetates and arylacetic acids via oxidative decarboxylative cyclization. 18 As a continuous study on this field, we visualized that 2,5-disubstituted 1,3,4-oxadiazoles could be synthesized from aryl hydrazides and arylacetic acids via dual oxidation using oxygen as the sole terminal oxidant. This reaction involves copper-catalyzed oxidative decarboxylation coupling followed by the oxidative functionalization of the imine C–H bond ( Scheme 1 e).…”

TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation

“…15,16,19 Among these, the synthetic routes for the synthesis of symmetrical TAPs not only involve the Chichibabin reaction but also methods with fixed nitrogen on starting materials such as benzylamines 20 or oxime acetates. 21 For the preparation of symmetrical TAPs, chalcones are usually applied as the starting material or paired with condensable synthons from various ammonia sources. 22 As shown in Scheme 1, Frank and Seven reported the revised Chichibabin reaction for the preparation of pyridines.…”