期刊
CHEMICAL SCIENCE
卷 13, 期 2, 页码 430-438出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc05257h
关键词
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资金
- Japan Society for the Promotion of Science (JSPS) via KAKENHI [17H06370, 18H03907, 20H04795, 21H01926]
- JST via CREST [JPMJCR19R1]
- JST via FOREST [JPMJFR201I]
- Institute for Chemical Reaction Design and Discovery (ICReDD)
- Grants-in-Aid for Scientific Research [17H06370, 20H04795, 21H01926, 18H03907] Funding Source: KAKEN
The study demonstrates the efficient palladium-catalyzed Sonogashira coupling of solid aryl halides using high-temperature ball milling, resulting in a variety of materials-oriented polyaromatic alkynes and the synthesis of novel luminescent materials. The utility of this method is further exemplified by the rapid synthesis of a fluorescent metal-organic framework precursor, showcasing the potential of Sonogashira coupling for the preparation of functional materials.
Sonogashira coupling represents an indispensable tool for the preparation of organic materials that contain C(sp)-C(sp(2)) bonds. Improving the efficiency and generality of this methodology has long been an important research subject in materials science. Here, we show that a high-temperature ball-milling technique enables the highly efficient palladium-catalyzed Sonogashira coupling of solid aryl halides that bear large polyaromatic structures including sparingly soluble substrates and unactivated aryl chlorides. In fact, this new protocol provides various materials-oriented polyaromatic alkynes in excellent yield within short reaction times in the absence of bulk reaction solvents. Notably, we synthesized a new luminescent material via the mechanochemical Sonogashira coupling of poorly soluble Vat Red 1 in a much higher yield compared to those obtained using solution-based conditions. The utility of this method was further demonstrated by the rapid synthesis of a fluorescent metal-organic framework (MOF) precursor via two sequential mechanochemical Sonogashira cross-coupling reactions. The present study illustrates the great potential of Sonogashira coupling using ball milling for the preparation of materials-oriented alkynes and for the discovery of novel functional materials.
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