Regioselective Catalytic and Stepwise Routes to Bulky,Functional‐Group‐Appended,and Luminescent 1,2‐Azaborinines |
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Authors: | Marius Schäfer Julian Schäfer Dr. Rian D. Dewhurst Dr. William C. Ewing Mirjam Krahfuß Maximilian W. Kuntze‐Fechner Marius Wehner Prof. Dr. Christoph Lambert Prof. Dr. Holger Braunschweig |
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Affiliation: | 1. Institut für Anorganische Chemie, Julius-Maximilians Universit?t Würzburg, Würzburg, Germany;2. http://www.braunschweiggroup.dehttp://www‐organik.chemie.uni‐wuerzburg.de/lehrstuehlearbeitskreise/lambert/home/;3. Wilhelm Conrad R?ntgen Research Center for Complex Material Systems, Institut für Organische Chemie, Julius-Maximilians Universit?t Würzburg, Würzburg, Germany |
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Abstract: | The regioselective syntheses of 1,2‐azaborinines is achieved using an unsymmetrical iminoborane through both catalytic and stepwise modular routes. The 1,2‐azaborinine ring can be selectively functionalized in the 4‐ and/or 6‐position through control of the stepwise reaction sequence, allowing access to vinyl‐functionalized and redox‐active, luminescent, donor‐functionalized 1,2‐azaborinines. The electrochemistry and photochemistry of a tetraarylamine‐substituted 1,2‐azaborinine are studied. Cyclic voltammetry of this compound, relative to a non‐B,N‐substituted reference molecule, showed an additional oxidation wave assigned to the oxidation of the azaborinine ring, while emission spectroscopy indicated that the azaborinine was significantly more fluorescent than the reference. |
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Keywords: | azaborete ligands azaborinines boron isosterism heterocycles |
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