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  • boron (1)
  • borylation (1)
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  • hydroarylation (1)
  • small HOMO-LUMO gap (1)

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Engineering a Small HOMO-LUMO Gap and Intramolecular B–B Hydroarylation by Diborene/Anthracene Orbital Intercalation (2017)
Wang, Sunewang R. ; Arrowsmith, Merle ; Böhnke, Julian ; Braunschweig, Holger ; Dellermann, Theresa ; Dewhurst, Rian D. ; Kelch, Hauke ; Krummenacher, Ivo ; Mattock, James D. ; Müssig, Jonas H. ; Thiess, Torsten ; Vargas, Alfredo ; Zhang, Jiji
The diborene 1 was synthesized by reduction of a mixture of 1,2-di-9-anthryl-1,2-dibromodiborane(4) (6) and trimethylphosphine with potassium graphite. The X-ray structure of 1 shows the two anthryl rings to be parallel and their π(C\(_{14}\)) systems perpendicular to the diborene π(B=B) system. This twisted conformation allows for intercalation of the relatively high-lying π(B=B) orbital and the low-lying π* orbital of the anthryl moiety with no significant conjugation, resulting in a small HOMO-LUMO gap (HLG) and ultimately an unprecedented anthryl B–B bond hydroarylation. The HLG of 1 was estimated to be 1.57 eV from the onset of the long wavelength band in its UV–vis absorption spectrum (THF, λ\(_{onset}\) = 788 nm). The oxidation of 1 with elemental selenium afforded diboraselenirane 8 in quantitative yield. By oxidative abstraction of one phosphine ligand by another equivalent of elemental selenium, the B–B and C\(^1\)–H bonds of 8 were cleaved to give the cyclic 1,9-diboraanthracene 9.
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