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An Umpolung Approach to Acyclic 1,4-Dicarbonyl Amides via Photoredox-Generated Carbamoyl Radicals

A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron-poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass-efficient formation of 1,4-dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally-friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal-free photocatalyst and a sustainable, non-toxic solvent system.

 

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The passage describes a method for generating and reacting carbamoyl radicals from oxamate salts, followed by reacting them with electron-poor olefins. The oxamate salt serves as a reductive quencher in the photoredox catalytic cycle, enabling the mild and mass-efficient formation of 1,4-dicarbonyl products, which is a challenging transformation in the context of functionalized amide formation. The use of ab initio calculations has helped to provide a better understanding of the process, which has been supported by experimental observations.

The method is designed to be environmentally friendly, using sodium as a cheap and low mass counterion, a metal-free photocatalyst, and a sustainable, non-toxic solvent system. Overall, the method offers a promising approach for the mass-efficient and mild formation of 1,4-dicarbonyl products, with potential applications in the synthesis of functionalized amides.

Related Products

Cat.No. Product Name Information
S6871 Sodium oxamate Sodium oxamate (SO, Aminooxoacetic acid, Oxamic acid) is an inhibitor of lactate dehydrogenase (LDH) that specificly inhibits LDH‑A. Sodium oxamate (SO) induces G2/M cell cycle arrest via downregulation of the CDK1/cyclin B1 pathway and promotes apoptosis through enhancement of mitochondrial ROS generation.

Related Targets

CDK LDH ROS Apoptosis related