Introducing the Dihydro-1,3-azaboroles: Convenient Entry by a Three-Component Reaction, Synthetic and Photophysical Application
Jun Li, Constantin G. Daniliuc, Kalathil K. Kartha, Gustavo Fernández, Gerald Kehr, Gerhard Erker
Abstract
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.
Topics & Concepts
ChemistryAcetyleneReagentDeprotonationComponent (thermodynamics)Ligand (biochemistry)Combinatorial chemistryFluorescencePhotochemistryOrganic chemistryBiochemistryQuantum mechanicsReceptorIonPhysicsThermodynamicsOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques