- Palladium/copper Co-catalyzed oxidative C-H/C-H carbonylation of diphenylamines: A way to access acridones
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An efficient palladium/copper co-catalyzed oxidative double C(sp2)-H functionalization/carbonylation of diphenylamines for synthesis of acridones has been developed. This method utilizes readily available starting materials and mild reaction conditions. The protocol provides a simple, efficient, and atomeconomic way to access acridones. Notably, the present protocol has excellent functional group tolerance and application value.
- Wen, Jiangwei,Tang, Shan,Zhang, Fan,Shi, Renyi,Lei, Aiwen
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- Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones
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Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C–N bond, CO extrusion, Cu migration, reductive elimination and DMSO-aided proton migration processes, involving multiple types of bond cleavage and formation in a single chemical step.
- Wu, Hao,Ma, Nana,Song, Mengxiao,Zhang, Guisheng
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- Method for synthesizing acridone derivatives by means of palladium-copper co-catalysis
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The invention discloses a method for synthesizing acridone derivatives by means of palladium-copper co-catalysis. The method comprises the steps that on the condition that palladium chloride, copper pivalate and di-tert-butyl peroxide or oxygen co-exist, diphenylamine compounds including symmetric diphenylamine and asymmetric diphenylamine are dissolved in an anhydrous organic solvent, all the materials are mixed to be uniform, a reaction is conducted for 20 h to 30 h under the condition of 80 DEG C to 120 DEG C in a carbon monoxide atmosphere, separation and purification are conducted, and the acridone derivatives can be obtained. According to the method for synthesizing the acridone derivatives by means of palladium-copper co-catalysis, the preparation method is simple, the diphenylamine compounds which are simple and easy to obtain are used as the raw materials, and the acridone derivatives are directly constructed through C-H/C-H oxidative carbonylation; the preparation condition is mild, and the target product can be obtained in a high-selectivity mode at 80 DEG C to 120 DEG C; the acridone derivatives have good substrate applicability, the range of substrates is greatly expanded, and the acridone derivatives have a great application prospect in biological medicine and materials and the like.
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Paragraph 0034; 0035; 0036; 0037
(2017/02/09)
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