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光诱导、苯肼促进的芳基氟化物、氯化物、溴化物和碘化物的无过渡金属脱卤反应

Photo-Induced, Phenylhydrazine-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides.

作者信息

Zhu Yiwei, Wu Zhimin, Sun Hongcai, Ding Junjun

机构信息

School of Chemistry and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, China.

出版信息

Molecules. 2023 Oct 3;28(19):6915. doi: 10.3390/molecules28196915.

DOI:10.3390/molecules28196915
PMID:37836758
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10574415/
Abstract

In this study, we present a straightforward and highly effective photo-triggered hydrogenation method for aryl halides, devoid of transition-metal catalysts. Through the synergistic utilization of light, PhNHNH, and a base, we have successfully initiated the desired radical-mediated hydrogenation process. Remarkably, utilizing mild reaction conditions, a wide range of aryl halides, including fluorides, chlorides, bromides, and iodides, can be selectively transformed into their corresponding (hetero)arene counterparts, with exceptional yields. Additionally, this approach demonstrates a remarkable compatibility with diverse functional groups and heterocyclic compounds, highlighting its versatility and potential for use in various chemical transformations.

摘要

在本研究中,我们提出了一种用于芳基卤化物的直接且高效的光触发氢化方法,该方法无需过渡金属催化剂。通过光、苯肼(PhNHNH)和碱的协同作用,我们成功启动了所需的自由基介导的氢化过程。值得注意的是,利用温和的反应条件,包括氟化物、氯化物、溴化物和碘化物在内的多种芳基卤化物均可选择性地转化为其相应的(杂)芳烃,产率优异。此外,该方法对各种官能团和杂环化合物具有显著的兼容性,突出了其在各种化学转化中的通用性和应用潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/8fe472b5a1db/molecules-28-06915-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/ca50abc79658/molecules-28-06915-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/74f31a109ebc/molecules-28-06915-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/2c613e0a9791/molecules-28-06915-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/c036d64acd5d/molecules-28-06915-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/8fe472b5a1db/molecules-28-06915-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/ca50abc79658/molecules-28-06915-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/74f31a109ebc/molecules-28-06915-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/2c613e0a9791/molecules-28-06915-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/c036d64acd5d/molecules-28-06915-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31d6/10574415/8fe472b5a1db/molecules-28-06915-sch005.jpg

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