%0 Generic %A Kinoshita, Hidenori %A Hirai, Nobuyoshi %A Miura, Katsukiyo %D 2014 %T Diisobutylaluminum Hydride Promoted Cyclization of o‑(Trimethylsilylethynyl)styrenes to Indenes %U https://acs.figshare.com/articles/dataset/Diisobutylaluminum_Hydride_Promoted_Cyclization_of_i_o_i_Trimethylsilylethynyl_styrenes_to_Indenes/2257435 %R 10.1021/jo501383v.s002 %2 https://acs.figshare.com/ndownloader/files/3893425 %K intramolecular carboalumination %K R 1 %K R 3 %K alkenylaluminum %K alkynyl moiety %K benzofulvene %K reaction mixture %K 3Si R 2 %K trimethylsilyl %K Diisobutylaluminum Hydride Promoted Cyclization %K cyclization mechanism %K substrate %K benzaldehyde %K diisobutylaluminum hydride %K regioselective hydroalumination %K IndenesThe reaction %K isomerization %X The reaction of o-(trimethylsilylethynyl)­styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerization of the alkenylaluminums formed, and intramolecular carboalumination. With substrates bearing a 2-(trimethylsilyl)­ethenyl group (R1 = Me3Si, R2 = R3 = H), bis-silylated benzofulvenes are obtained upon treatment of the reaction mixture with an excess amount of benzaldehyde. %I ACS Publications