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通过1,5-氢原子转移实现的杂芳烃与仲胺的光氧化还原交叉脱氢C(sp)-C(sp)偶联反应

Photoredox cross-dehydrogenative C(sp)-C(sp) coupling of heteroarenes with secondary amines through 1,5-HAT.

作者信息

Srinivasu Vinjamuri, Pattanaik Swadhin, Sureshkumar Devarajulu

机构信息

Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, West Bengal, India.

Department of Chemical Sciences, Indian Institute of Science Education and Research, Berhampur-760010, Odisha, India.

出版信息

Chem Commun (Camb). 2024 Sep 5;60(72):9757-9760. doi: 10.1039/d4cc02818j.

Abstract

The functionalization of α-C(sp)-H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis α-C(sp)-H bond functionalization in alicyclic and aliphatic secondary amines facilitated by intramolecular 1,5-hydrogen atom transfer (HAT). This finding unlocks a sustainable method for rapidly constructing complex heterocyclics cross-dehydrogenative C-C coupling of protected amines and nitrogen-containing heterocycles. This protocol boasts broad applicability to various substrates, exhibits tolerance to numerous functional groups, and supports the late-stage modification of drug molecules.

摘要

胺类中α-C(sp)-H键的官能团化已成为当代研究的一个焦点。在此,我们报道了一种利用光催化实现脂环族和脂肪族仲胺中α-C(sp)-H键官能团化的新方法,该方法由分子内1,5-氢原子转移(HAT)促进。这一发现开启了一种可持续的方法,用于快速构建复杂杂环——受保护胺与含氮杂环的交叉脱氢C-C偶联。该方案对各种底物具有广泛的适用性,对众多官能团具有耐受性,并支持药物分子的后期修饰。

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