通过位置选择性1,5-氢原子转移级联，光氧化还原催化甘氨酸衍生物和多肽的三组分烷基化

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-04-02 DOI:10.1039/d5qo00294j

Hongying Fan , Liulin Jiao , Ting Yuan , Jian Chen , Qingyun Gu , Xue Zhang , Jinyu Hou , Zhongzhen Yang , Li Guo , Yong Wu

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引用次数: 0

摘要

我们报道了一种可见光介导的三组分反应，通过n中心自由基介导的1,5-氢原子转移结合烯烃与烷基自由基的位点选择性远端C(sp3) -H交叉偶联反应，使甘氨酸衍生物和肽的α-C(sp3) -H烷基化。该方法实现了烯烃的双功能化，为多肽衍生生物活性化合物的模块化合成提供了一条有前途的替代途径。此外，这种转化的潜在合成价值在多肽的放大反应和后期功能化中得到了证明。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photoredox-catalyzed three-component alkylation of glycine derivatives and peptides via a site-selective 1,5-hydrogen atom transfer cascade†

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Photoredox-catalyzed three-component alkylation of glycine derivatives and peptides via a site-selective 1,5-hydrogen atom transfer cascade†

We report a visible-light-mediated three-component reaction via N-centered radical-mediated 1,5-hydrogen atom transfer combined with site-selective remote C(sp³)–H cross-coupling reactions of alkenes with alkyl radicals for the α-C(sp³)–H alkylation of glycine derivatives and peptides. This protocol performs the double functionalization of alkenes and provides a promising alternative route for the modular synthesis of peptide-derived bioactive compounds. Additionally, the potential synthetic value of this transformation is demonstrated in the scale-up reactions and late-stage functionalization of peptides.

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来源期刊

Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

自引率

0.00%

发文量