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Regioselective Synthesis of 5‑Metalated 2‑Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

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posted on 2019-10-17, 18:36 authored by Tetsuji Yata, Yuji Kita, Yoshihiro Nishimoto, Makoto Yasuda
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).

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