An efficient and general aerobic oxidative coupling method to prepare 1,1′-binaphthyl-2,2′-diamines (BINAMs) from N-substituted-2-aminonaphthalene (1) based on [Fe^III(cyclen)(Cl)₂]Cl catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) at room temperature is reported. The highly selective conditions were applied to prepare a list of N,N′-dialkyl-, N,N′-dibenzyl-, and N,N′-diaryl-BINAMs with moderate to high yields. Based on mechanistic studies, which include control experiments and variable time normalization analysis, it is suggested that the coupling between [Fe^III(cyclen)(1)(OOH)]⁺² and 2-aminonaphthalene 1 is the key irreversible step in the catalytic cycle.

中文翻译：

---

均相非血红素铁催化剂对 2-氨基萘的有氧氧化偶联


一种高效、通用的有氧氧化偶联方法，以[Fe ^III (cyclen)为原料，由N-取代-2-氨基萘(1)制备1,1'-联萘-2,2'-二胺(BINAMs)据报道，室温下 1,1,1,3,3,3-六氟丙-2-醇 (HFIP) 中的 )(Cl) ₂ ]Cl 催化剂。应用高选择性条件以中等到高产率制备一系列 N,N'-二烷基-、N,N'-二苄基-和 N,N'-二芳基-BINAM。基于机理研究，包括控制实验和可变时间归一化分析，建议 [Fe ^III (cyclen)(1)(OOH)] ⁺² 和 2 之间的耦合-氨基萘1是催化循环中关键的不可逆步骤。