%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