Introducing the Dihydro-1,3-azaboroles: Convenient Entry by a Three-Component Reaction, Synthetic and Photophysical Application
2021
Li, Jun | Daniliuc, Constantin G. | Kartha, Kalathil K. | Fernández, Gustavo | Kehr, Gerald | Erker, Gerhard
The (Fmes)BH₂·SMe₂ reagent (7) reacts sequentially with an acetylene and, e.g., xylylisonitrile in a convenient three-component reaction to give a series of unprecedented dihydro-1,3-azaborole derivatives 16. The tolane-derived example 16a was deprotonated and used as a ligand in organometallic chemistry. Compounds 16 served as the starting materials for the straightforward synthesis of various dihydro-1,3-azaborinine derivatives by treatment with an isonitrile. Several diaryldihydro-1,3-azaboroles showed interesting photophysical properties such as aggregation-induced emission and high fluorescence quantum yields.
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