We report the Ni-catalyzed Suzuki–Miyaura coupling of aliphatic amide derivatives. Prior studies have shown that aliphatic amide derivatives can undergo Ni-catalyzed carbon–heteroatom bond formation but that Ni-mediated C–C bond formation using aliphatic amide derivatives has remained difficult. The coupling disclosed herein is tolerant of considerable variation with respect to both the amide-based substrate and the boronate coupling partner and proceeds in the presence of heterocycles and epimerizable stereocenters. Moreover, a gram-scale Suzuki–Miyaura coupling/Fischer indolization sequence demonstrates the ease with which unique polyheterocyclic scaffolds can be constructed, particularly by taking advantage of the enolizable ketone functionality present in the cross-coupled product. The methodology provides an efficient means to form C–C bonds from aliphatic amide derivatives using nonprecious-metal catalysis and offers a general platform for the heteroarylation of aliphatic acyl electrophiles.

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脂肪族酰胺的镍催化铃木-宫浦联轴器

我们报告了镍催化的脂族酰胺衍生物的Suzuki-Miyaura偶联。先前的研究表明，脂族酰胺衍生物可以经历Ni催化的碳-杂原子键的形成，但是使用脂族酰胺衍生物形成Ni介导的C-C键仍然很困难。本文公开的偶联相对于基于酰胺的底物和硼酸酯偶联配偶体都容许相当大的变化，并且在存在杂环和可差向异构的立体中心的情况下进行。此外，克级的Suzuki-Miyaura偶联/ Fischer吲哚化序列证明了构建独特的多杂环支架的简便性，特别是利用了交叉偶联产物中存在的可烯化的酮官能团。