10.1021/jo501383v.s002
Hidenori Kinoshita
Hidenori
Kinoshita
Nobuyoshi Hirai
Nobuyoshi
Hirai
Katsukiyo Miura
Katsukiyo
Miura
Diisobutylaluminum Hydride
Promoted Cyclization of <i>o</i>‑(Trimethylsilylethynyl)styrenes to Indenes
American Chemical Society
2014
intramolecular carboalumination
R 1
R 3
alkenylaluminum
alkynyl moiety
benzofulvene
reaction mixture
3Si R 2
trimethylsilyl
Diisobutylaluminum Hydride Promoted Cyclization
cyclization mechanism
substrate
benzaldehyde
diisobutylaluminum hydride
regioselective hydroalumination
IndenesThe reaction
isomerization
2014-09-05 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Diisobutylaluminum_Hydride_Promoted_Cyclization_of_i_o_i_Trimethylsilylethynyl_styrenes_to_Indenes/2257435
The
reaction of <i>o</i>-(trimethylsilylethynyl)styrenes with
diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1<i>H</i>-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 (R<sup>1</sup> = Me<sub>3</sub>Si, R<sup>2</sup> = R<sup>3</sup> = H), bis-silylated
benzofulvenes are obtained upon treatment of the reaction mixture
with an excess amount of benzaldehyde.