Here we present the highly effective cleavage of C–C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate with a γ-OH group will lead to the formation of C-2 monosubstituted oxazole. A one-pot process involving the BR reaction and hydrolysis has also been developed to directly afford an up to 96% total yield of benzonitriles, benzamides, and anilines. This strategy enabled us to successfully apply the BR reaction to the degradation of lignin model compounds to N-functionalized aromatic products under mild conditions.

中文翻译：

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通过贝克曼重排将木质素模型化合物转化为N-取代的芳族化合物

这里，我们提出的C-C键的高度有效的裂解在木质素模型化合物用于生产ñ -取代的芳族化合物在高达96％的总收率，包括苄腈和酰胺，经由肟形成随后贝克曼重排（BR）。酰胺可以分别进一步水解为苯胺（产率> 92％）和羧酸（> 90％）。另外，使用具有γ-OH基团的底物将导致形成C -2单取代的恶唑。还开发了一种涉及BR反应和水解的一锅法，可直接提供高达96％的苯甲腈，苯甲酰胺和苯胺总产率。这种策略使我们能够成功地将BR反应应用于木质素模型化合物的降解在温和条件下经过N-官能化的芳族产品。