jo9b02186_si_001.pdf (2.83 MB)
Regioselective Synthesis of 5‑Metalated 2‑Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide
journal contribution
posted on 2019-10-17, 18:36 authored by Tetsuji Yata, Yuji Kita, Yoshihiro Nishimoto, Makoto YasudaThe
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).