Dominika Kobus-Bartoszewicz, Mariusz Zalewski, Krzysztof Melcer, Mikołaj Warda, Sebastian Stecko
{"title":"Photoinduced metal‐free hydrocarboxylation of allylamines","authors":"Dominika Kobus-Bartoszewicz, Mariusz Zalewski, Krzysztof Melcer, Mikołaj Warda, Sebastian Stecko","doi":"10.1002/adsc.202401326","DOIUrl":null,"url":null,"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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"50 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401326","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
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.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
