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Vicinal Vinylation of Boron-Doped Acenes via Heck Coupling
Maurice Metzler1, Michael Bolte1, Alexander Virovets1
1Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Straße 7, D-60438 Frankfurt (Main), Germany.
Abstract:
Silylated and halogenated benzenes 1,2-(Me3Si)2-4,5-X2-C6H2 [X = Br (3), I (4)] are versatile synthetic building blocks. 3 was prepared from known 1,2-(Me3Si)2-4,5-Cl2-C6H2 via C-Cl borylation/bromodeboronation; CuI-catalyzed Br/I exchange on 3 affords 4. 3 or 4 and BBr3 yield 9,10-dibromo-9,10-dihydro-9,10-diboraanthracenes (DBAs) 7 or 8. The B centers were protected with mesityl (Mes; 9, 10) or 2,4,6-tris(trifluoromethyl)phenyl (FMes; 11, 12) groups. Heck coupling of 9 and styrene/2,3,4,5,6-pentafluorostyrene furnishes the two tetravinyl-substituted green/blue emitters 13/14.
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