Yata Tetsuji, Kita Yuji, Nishimoto Yoshihiro, Yasuda Makoto
Department of Applied Chemistry, Graduate School of Engineering , Osaka University , 2-1 Yamadaoka , Suita, Osaka 565-0871 , Japan.
Frontier Research Base for Global Young Researchers, Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering , Osaka University , 2-1 Yamadaoka , Suita, Osaka 565-0871 , Japan.
J Org Chem. 2019 Nov 1;84(21):14330-14341. doi: 10.1021/acs.joc.9b02186. Epub 2019 Oct 17.
The oxyindation of carbonyl-ene-yne compounds with indium trihalides proceeded efficiently to give di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrone and a zwitterion intermediate were identified by X-ray crystallographic analysis. The application of organoindium compounds to oxidation or cross-coupling provided easy access to various multifunctionalized 2-pyrones. Some 2-pyrone derivatives show intense fluorescence only in the solid state (aggregation-induced emission).
羰基烯炔化合物与三卤化铟的氧代反应高效进行，生成带有碳 - 铟键的二取代、三取代和四取代的2 - 吡喃酮。通过X射线晶体学分析鉴定了金属化的2 - 吡喃酮和两性离子中间体。有机铟化合物在氧化或交叉偶联中的应用为获得各种多功能化的2 - 吡喃酮提供了便利途径。一些2 - 吡喃酮衍生物仅在固态时显示出强烈的荧光（聚集诱导发光）。
