Abstract
Bis(3-methylindolyl)-2-(1-methylimidazolyl)methane (1) was synthesized by acid-catalyzed condensation of methyl-2-formylimidazole and two equivalents of 3-methylindole, followed by deprotonation of the imidazole moiety of the protonated compound, [(1-CH3C3H2N2H)HC(3-CH3C8H4NH)2][HSO4] ([1•H][HSO4 ]). Reactions of a trialkylaluminum or tri‑tert-butylgallium with 1 produced complexes (1-CH3C3H2N2)HC(3-CH3C8H4N)(3-CH3C8H4NH)MR2 (M = Al, R = Me (2a), Et (2b), iBu (2c), tBu (2d); M = Ga, R = tBu (3)) in which mono-deprotonated 1 adopts a bidentate coordination mode. Thermolysis of 2a-2d or 3 in refluxing toluene did not result in further alkane elimination. Deprotonation of 1 with two equivalents of nBuLi followed by reaction with an alkylaluminum dichloride yielded monomeric, tripodal complexes (1-CH3C3H2N)HC(3-CH3C8H4N)2MR (M = Al, R = Me (4a), Et (4b), iBu (4c), tBu (4d)) in which bis-deprotonated 1 adopts a tridentate coordination mode. Reaction of 1 with two equivalents of trimethylaluminum or triethylaluminum yields dialuminum complexes (1-CH3C3H2N)HC(3-CH3C8H4N)2Al2R4 (R = Me (5a), Et (5b). In addition to NMR (1H, 13C) spectroscopy, compounds 1, 2d, 3, and 4b were further characterized by X-ray crystallography as CH2Cl2 or toluene solvates.
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