A TEMPO-promoted method was developed for the synthesis of symmetric bis-N-Mannich bases via sequential activation of two α,α′-amino C(sp³)–H bonds of N,N-dimethylanilines under mild conditions. This methodology was further extended for monoimidation of α-amino-functionalized methylanilines to give unsymmetric N-Mannich bases in good to high yields. Several control experiments were performed, and the coupling reaction outcomes indicated that the oxoammonium (TEMPO⁺) species is involved in the reaction.

中文翻译：

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TEMPO 促进叔苯胺的单亚胺化和双亚胺化：对称和不对称 N-曼尼希碱基的合成

开发了一种 TEMPO 促进的方法，用于在温和条件下通过顺序激活N , N-二甲基苯胺的两个 α,α'-氨基 C(sp ³ )-H 键来合成对称双-N-曼尼希碱基。该方法进一步扩展用于 α-氨基官能化甲基苯胺的单酰亚胺化，以良好至高产率提供不对称N-曼尼希碱。进行了几个对照实验，偶联反应结果表明氧铵 (TEMPO ⁺ ) 物质参与了反应。