使用三卤化铟通过羰基烯炔化合物的分子内氧金属化反应区域选择性合成5-金属化的2-吡喃酮。
Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide.
作者信息
Yata Tetsuji, Kita Yuji, Nishimoto Yoshihiro, Yasuda Makoto
机构信息
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.
出版信息
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）。
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