Iminium and azonium-activated metal and oxidant-free C–H functionalization of aliphatic amines,Chemical Communications

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Iminium and azonium-activated metal and oxidant-free C–H functionalization of aliphatic amines
Chemical Communications ( IF 4.3 ) Pub Date : 2023-06-09 , DOI: 10.1039/d3cc01299a
Nandini Ray ₁ , Chandan K Jana ₁

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A wide variety of synthetic methods have been developed for the synthesis of functionalized aliphatic amines because of their broad utility in both synthetic and medicinal chemistry. The synthesis of functionalized aliphatic amines via direct C–H functionalization of readily available aliphatic amines, the majority of which rely on the use of metallic reagents/catalysts and hazardous oxidants, is advantageous in comparison to the classical multistep approaches. However, the scope to carry out such direct C–H functionalization of aliphatic amines under metal and oxidant-free conditions is being continuously explored. As a result, the examples of C–H functionalization of aliphatic amines employing iminium/azonium ions, which are formed via classical condensation of amines and carbonyl/nitroso compounds, are on the rise. This article summarizes the recent developments in the iminium and azonium-activated metal and oxidant-free C–H functionalization of aliphatic amines with the main focus on the intermolecular reactions of iminium/azonium ions, enamines, and zwitterions with suitable nucleophiles, electrophiles and dipolarophiles.

中文翻译：

亚胺和氮激活的金属和无氧化剂的脂肪胺 C-H 官能化

由于功能化脂肪胺在合成化学和药物化学中的广泛用途，已经开发了多种合成方法来合成官能化脂肪胺。通过对容易获得的脂肪胺进行直接 C-H 官能化来合成官能化脂肪胺，其中大部分依赖于使用金属试剂/催化剂和危险氧化剂，与经典的多步方法相比具有优势。然而，在无金属和氧化剂的条件下对脂肪胺进行这种直接C-H官能化的范围正在不断探索。因此，使用亚胺/氮离子对脂肪胺进行 C-H 官能化的例子，这些离子是通过胺和羰基/亚硝基化合物的经典缩合反应正在兴起。本文总结了亚胺和氮激活金属以及脂肪胺无氧化剂C-H官能化的最新进展，主要关注亚胺/氮离子、烯胺和两性离子与合适的亲核试剂、亲电试剂和亲偶极试剂的分子间反应。

更新日期：2023-06-09

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