Progress in Cu-catalyzed carbon-heteroatom bond forming reactions

Recently, we reported that some very cheap and conveniently available N-aryl-N’-alkyl substituted oxalamides are powerful ligands to promote Cu-catalyzed coupling between (hetero)aryl chlorides and phenols, leading to the formation of a great variety of diaryl ethers in good to excellent yields at 120 oC (Angew. Chem. Int. Ed. 2016, 55, 6211). A board range of functional groups are tolerated, which include amines, alcohols, amides, halides, esters, ketones, nitriles, as well as a number of heterocycles. This new catalytic system could be used for preparing insecticides diafenthiuton, permethrin, cypermethrin and deltamethrin from suitable aryl chlorides, and thereby providing a more economic approach for manufacturing these chemicals.

This work is an extension of the studies on copper-catalyzed coupling reactions from our group. Last year, we revealed that some N,N’-diaryl substituted oxalamides were effective ligands for copper-catalyzed aryl amination with (hetero)aryl chlorides (J. Am. Chem. Soc. 2015, 137, 11942; Org. Lett. 2015, 17, 5934). Since substituted aniline and diaryl ether are common moieties for a large number of pharmaceutical products, agrochemicals and materials, these newly developed reactions will definitely find applications in producing the functional molecules, which represents a big breakthrough in the area of metal-catalyzed coupling reactions.

These projects were sponsored by the National Natural Science Foundation of China and Chinese Academy of Sciences. 

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