Copper(II)-Catalyzed Direct Amination of 1-Naphthylamines at the C8 Site

Abstract

A new and simple protocol for C8–H amination of 1-naphthylamine derivatives was developed using copper salt and di-tert-butyl peroxide (DTBP) as the catalyst and oxidant, respectively. This reaction proceeded smoothly under the additive and solvent-free conditions. In addition, this amination showed excellent regioselectivity and could tolerate various functional groups.

Silver(I) Promoted the C4–H Bond Phosphonation of 1-Naphthylamine Derivatives with H-Phosphonates

“…The resulting residue was purified by column chromatography (hexane/ethyl acetate = 3:1) (v/v) to afford the pure product 1a as a white solid (4.47 g, 90%). Amides 1b–x were prepared from the corresponding pyridine carboxylic acids and 1-naphthylamine according to the reported procedure. , …”

“…In recent years, the research interest of our group mainly focused on N–N bidentate chelation-directed C–H functionalization of arene derivatives, especially for the 8-aminoquinoline derivatives and 1-naphthylamine derivatives. , Inspired by these previous discoveries, we herein described a simple protocol for silver­(I)-promoted regioselective phosphonation of 1-naphthylamides at the C4 site using H-phosphonates as the phosphonating reagent (Scheme c).…”

Cobalt‐Catalyzed C(sp2)−O Bond Formation by Directing Group Assisted C−H Activation

“…1‐Naphthylamine and its derivatives have been widely studied as pharmaceutical [35] and functional materials [36] . Their functionalization is attractive to synthetic chemists; notably, C8 functionalization of 1‐naphthylamine analogs containing directing groups has been conducted using transition metal catalysts such as Pd [37] and Cu [38] . Although research is focused on C−C and C−N bond‐forming reactions, C−O bond formation, such as the alkoxylation of 1‐naphthylamine analogues, has also been studied.…”

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

“…除此之外, 张三奇课题组 [36] 以 2-氨基苯 基-2-吡啶作为导向基实现了铜催化芳基碳氢键胺化反 应(Scheme 16, c). 2020 年, 吴养洁课题组 [37] 以醋酸铜为 催化剂, 过氧化二叔丁基(DTBP)为氧化剂, 实现了 1-萘 胺 C(8)位碳氢键胺化反应(Scheme 16, d). 值得一提的 是, 该反应可在无添加剂、无溶剂的条件下进行.…”