绿色反应介质中铜催化吲哚和吡咯n -芳基化的外部无碱方法

IF 4.3 2区 化学 Q2 CHEMISTRY, APPLIED Applied Organometallic Chemistry Pub Date : 2025-01-01 DOI:10.1002/aoc.7966
Mohendra Tahu, Dipika Konwar, Dibyashree Dolakasharia, Utpal Bora
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引用次数: 0

摘要

n -芳基化杂环分子被广泛发现是许多药物和农用化合物的关键成分。本文开发了一种廉价的1,10-菲罗啉辅助铜催化的可持续绿色方法,用于在商业碱和无添加剂条件下进行吲哚和吡咯的n -芳基化。废弃生物质衍生的香蕉皮灰水提取物(WEB)被用作安全的反应介质和碱,而不是危险的溶剂,因此,目前的绿色方案已经实现了环境友好的形象。吡咯与碘化芳基、电子多样性吲哚与碘化芳基/溴化芳基在100℃下以CuI为催化剂、1,10-菲罗啉为配体、WEB为碱和溶剂的存在下反应,在12 h内生成n -芳基化产物。吲哚与芳基碘化物的反应收率可达93%,而芳基溴的反应收率可达54%。利用废弃生物质衍生物进行有机转化反应是本方案的关键步骤,符合绿色化学的目标。
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External Base-Free Approach for Copper-Catalyzed N-Arylation of Indoles and Pyrroles in Green Reaction Medium

N-Arylated heterocyclic molecules are extensively found as key components in numerous pharmaceutical and agrochemical compounds. Herein, inexpensive 1,10-phenanthroline-assisted copper-catalyzed sustainable greener methodology has been developed for N-arylation of indoles and pyrrole under commercial base and additive-free conditions. Waste biomass–derived water extract of banana peel ash (WEB) has been used as safe reaction medium and base instead of hazardous solvents, and hence, the current green protocol has achieved an environmentally benign profile. Reaction of pyrrole with aryl iodides and electronically diverse indoles with aryl iodides/aryl bromides in the presence of CuI as catalyst, 1,10-phenanthroline as ligand, and WEB as a base and solvent at 100°C has furnished N-arylated product within 12 h. Reaction of indoles with aryl iodides furnished up to 93% yields while aryl bromides resulted in up to 54% yield of the desired product. The utilization of waste biomass derivative for organic transformation reaction is the key step of this protocol, which is in consistence with the goals of green chemistry.

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来源期刊
Applied Organometallic Chemistry
Applied Organometallic Chemistry 化学-无机化学与核化学
CiteScore
7.80
自引率
10.30%
发文量
408
审稿时长
2.2 months
期刊介绍: All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.
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