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Introducing the Dihydro-1,3-azaboroles: Convenient Entry by a Three-Component Reaction, Synthetic and Photophysical Application

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journal contribution
posted on 21.01.2021, 16:09 authored by Jun Li, Constantin G. Daniliuc, Kalathil K. Kartha, Gustavo Fernández, Gerald Kehr, Gerhard Erker
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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