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Cu/N,N'-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines.

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N,N'-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol… Click to show full abstract

N,N'-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For (hetero)aryl bromides/iodides, coupling reaction took place at 80-100 °C with 1 mol % CuI and 2 mol % DBO. A variety of heteroanilines worked well to afford the arylation products in good to excellent yields.

Keywords: arylation heteroanilines; hetero aryl; dibenzyloxalamide catalyzed; arylation; mol; catalyzed arylation

Journal Title: Organic letters
Year Published: 2019

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