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使用水合自由基阳离子对芳香胺进行无环境催化剂的氧化反应。

Ambient catalyst-free oxidation reactions of aromatic amines using water radical cations.

作者信息

Zhang Xiaoping, Hu Pinghua, Duan Minmin, Chingin Konstantin, Balabin Roman, Zhang Xinglei, Chen Huanwen

机构信息

Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology Nanchang 330013 P. R. China

School of Pharmacy, Jiangxi University of Chinese Medicine Nanchang 330004 P. R. China

出版信息

Chem Sci. 2024 Sep 6;15(39):16125-32. doi: 10.1039/d4sc04519j.

DOI:10.1039/d4sc04519j
PMID:39290584
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11403581/
Abstract

Water radical cations play a pivotal role in various scientific and industrial fields due to their unique reactivity and capacity to drive complex chemical transformations. Here we explored the formation of quaternary ammonium cations through the direct oxidation reaction of aromatic amines, facilitated by water radical cations within water microdroplets. This process was monitored mass spectrometry and occurs under ambient conditions, negating the need for traditional chemical catalysts or oxidants and achieving an impressive yield of approximately 80%. Additionally, we employed a multi-channel spray system and enhanced both the reactant concentration and flow rate, thereby enabling gram-scale synthesis. These findings not only demonstrate the effectiveness and eco-friendliness of microdroplet chemistry but also provide a new understanding of heterogeneous ˙OH generation channels, thereby boosting the synthetic efficiency and sustainability of chemical processes.

摘要

水合自由基阳离子因其独特的反应活性和驱动复杂化学转化的能力,在各种科学和工业领域中发挥着关键作用。在此,我们探索了在水微滴中由水合自由基阳离子促进的芳香胺直接氧化反应形成季铵阳离子的过程。该过程通过质谱监测,且在环境条件下发生,无需传统化学催化剂或氧化剂,产率约为80%,令人印象深刻。此外,我们采用了多通道喷雾系统,提高了反应物浓度和流速,从而实现了克级合成。这些发现不仅证明了微滴化学的有效性和环境友好性,还为非均相·OH生成通道提供了新的认识,从而提高了化学过程的合成效率和可持续性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/a3ff54dbc5c0/d4sc04519j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/aa4d78c654df/d4sc04519j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/529ccfaf70ef/d4sc04519j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/e695a60c8dea/d4sc04519j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/a3ff54dbc5c0/d4sc04519j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/aa4d78c654df/d4sc04519j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/529ccfaf70ef/d4sc04519j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/e695a60c8dea/d4sc04519j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a039/11463310/a3ff54dbc5c0/d4sc04519j-f4.jpg

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