FeCl3-Catalyzed Photochemical Reductive Transamidation of Nitroarenes: A Sustainable Approach Using Sacrificial C−H Bonds

IF 4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-02-25 DOI:10.1002/adsc.202401574
Karthik Rajan Rajamanickam, Minwoo Park, Kyungho Park, Sunwoo Lee
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Abstract

A sustainable photochemical reductive transamidation of nitroarenes catalyzed by FeCl3 under blue LED irradiation is reported. This method eliminates the need for pre-reduction steps or stoichiometric reducing agents by utilizing sacrificial C−H bonds from organic solvents. The reaction proceeds via FeCl3-catalyzed single-electron transfer (SET) and hydrogen atom transfer (HAT) cascades. A previously unreported intermediate formed between nitroarenes and N-methylpyrrolidone (NMP) is discovered, playing a crucial role in facilitating substitution with amides. The method exhibits broad functional group tolerance and achieves yields up to 82%, demonstrating compatibility with a wide range of nitroarenes and amides.

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fecl3催化硝基芳烃的光化学还原转酰胺:一种利用牺牲C-H键的可持续方法
报道了在蓝光LED照射下,FeCl3催化硝基芳烃的可持续光化学还原性转酰胺反应。该方法通过利用来自有机溶剂的牺牲C-H键,消除了预还原步骤或化学计量还原剂的需要。反应通过fecl3催化的单电子转移(SET)和氢原子转移(HAT)级联进行。在硝基芳烃和n -甲基吡咯烷酮(NMP)之间发现了一种以前未报道的中间体,在促进与酰胺的取代中起着至关重要的作用。该方法具有广泛的官能团耐受性,产率高达82%,证明了与多种硝基芳烃和酰胺的相容性。
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来源期刊
Advanced Synthesis & Catalysis
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.
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