An iron‐catalyzed protocol for the synthesis of 3‐amino‐3‐aminomethyl‐2‐oxindole heterocyclic structures is disclosed employing isatins and non‐nucleophilic N‐methoxybenzamides. This reaction class is associated with broad scope and tolerates numerous functionalities, such as fluoro, chloro, bromo, iodo, trifluoromethyl, nitrile, ester, ether, and alkenyl, including heteroaryl ‐ thiophene, benzothiophene, carbazolyl, indolyl, eugenol, and polycyclic cholesterol moieties. Detailed mechanistic investigations reveal that the reaction proceeds via iron‐catalyzed N‒O bond cleavage in N‐methoxybenzamides, generating formaldehyde and benzamide, and through the intermediacy of isatin‐ketimines and N‐(hydroxymethyl)benzamides. Overall, this amidation reaction involves one C‒C and two C‒N bond‐forming tandem processes, providing a range of β‐amino‐aminomethyl‐oxindoles (45 examples) in up to 88% yields.

中文翻译：

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铁催化的 C-C 和 C-N 键形成串联酰胺化提供了 3-Amino-3-Aminomethyl-2-Oxindole 框架

公开了使用靛红和非亲核N-甲氧基苯甲酰胺合成3-氨基-3-氨基甲基-2-羟吲哚杂环结构的铁催化方案。该反应类别涉及范围广泛，可耐受多种官能团，例如氟、氯、溴、碘、三氟甲基、腈、酯、醚和烯基，包括杂芳基噻吩、苯并噻吩、咔唑基、吲哚基、丁子香酚和多环胆固醇部分。详细的机理研究表明，该反应通过铁催化 N-甲氧基苯甲酰胺中的 N-O 键断裂，生成甲醛和苯甲酰胺，并通过靛红酮亚胺和 N-（羟甲基）苯甲酰胺作为中介进行。总体而言，该酰胺化反应涉及一个 C-C 和两个 C-N 键形成串联过程，提供一系列 β-氨基-氨基甲基-羟吲哚（45 个实例），产率高达 88%。