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通过使用二芳基碘鎓盐生成的芳炔中间体实现的 -芳基吡咯的狄尔斯-阿尔德环加成反应。

Diels-Alder cycloadditions of -arylpyrroles via aryne intermediates using diaryliodonium salts.

作者信息

Chen Huangguan, Han Jianwei, Wang Limin

机构信息

Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Beilstein J Org Chem. 2018 Feb 6;14:354-363. doi: 10.3762/bjoc.14.23. eCollection 2018.

DOI:10.3762/bjoc.14.23
PMID:29507640
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5815300/
Abstract

With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of -arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35-96%). Furthermore, with a catalytic amount of TsOH·HO, these amines can be converted into the corresponding -phenylamine derivatives easily, which are potentially useful in photosensitive dyes.

摘要

通过使用二芳基碘鎓盐形成苯炔的策略,报道了芳基吡咯与苯炔的环加成反应。已以中等至优异的产率(35 - 96%)合成了多种带有不同取代基的桥环胺。此外,在催化量的对甲苯磺酸一水合物存在下,这些胺可以轻松转化为相应的芳基苯胺衍生物,它们在光敏染料方面具有潜在用途。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/0ed8829a01fa/Beilstein_J_Org_Chem-14-354-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/b6c02d0092d8/Beilstein_J_Org_Chem-14-354-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/3f53129e5692/Beilstein_J_Org_Chem-14-354-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/0ed8829a01fa/Beilstein_J_Org_Chem-14-354-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/b6c02d0092d8/Beilstein_J_Org_Chem-14-354-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/3f53129e5692/Beilstein_J_Org_Chem-14-354-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff07/5815300/0ed8829a01fa/Beilstein_J_Org_Chem-14-354-g004.jpg

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Org Lett. 2017 Dec 1;19(23):6420-6423. doi: 10.1021/acs.orglett.7b03307. Epub 2017 Nov 16.
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Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature.伪环芳基苯并碘硼杂环戊烷:室温下水引发的高效苯炔前体
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Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights.
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Identification of anti-pathogenic activity among predicted small-molecule inhibitors of LasR or nitric oxide reductase (NOR).在预测的LasR或一氧化氮还原酶(NOR)小分子抑制剂中鉴定抗致病活性。
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