Photoinduced metal‐free hydrocarboxylation of allylamines

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-12-13 DOI:10.1002/adsc.202401326

Dominika Kobus-Bartoszewicz, Mariusz Zalewski, Krzysztof Melcer, Mikołaj Warda, Sebastian Stecko

引用次数: 0

Abstract

Herein, we disclose a new photochemical process to prepare γ‐amino acids from allylamines and formic acid salts. The investigated redox‐neutral hydrocarboxylation process produces high yields across a wide range of functionalized allylamine substrates with excellent regioselectivity. The developed operationally simple protocol can be readily scaled with low photocatalyst loading (from 1% up to 0.02 mol%) without the need for any precautions to exclude air or moisture. The mechanistic working model utilizes a thiol‐catalyzed radical chain process, delivering the hydrogen atom and CO2 from formic acid salt across the alkene substrate through the carboxylate radical (CO2•‐), a crucial reactive intermediate.

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在此，我们揭示了一种从烯丙胺和甲酸盐制备γ-氨基酸的新型光化学工艺。所研究的氧化还原中性加氢羧化工艺在广泛的功能化烯丙基胺底物中都能产生高产率，并且具有极佳的区域选择性。所开发的方案操作简单，可在低光催化剂负载量（从 1%到 0.02 摩尔%）条件下轻松扩展，无需采取任何排除空气或湿气的预防措施。机理工作模型利用硫醇催化的自由基链过程，通过羧酸自由基（CO2--）这一关键的反应中间体，将甲酸盐中的氢原子和二氧化碳传递到烯烃底物上。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.