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Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems
| Title: | Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems |
| Authors: | Gao, Yunpeng Browse this author | | Feng, Chi Browse this author | | Seo, Tamae Browse this author | | Kubota, Koji Browse this author | | Ito, Hajime Browse this author →KAKEN DB |
| Issue Date: | 2022 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Chemical science |
| Volume: | 13 |
| Issue: | 2 |
| Start Page: | 430 |
| End Page: | 438 |
| Publisher DOI: | 10.1039/d1sc05257h |
| Abstract: | 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. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/83902 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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