Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: an entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction.
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue.
Nakao
Yoshiaki
Y
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan. nakao@npc05.kuic.kyoto-u.ac.jp
Imanaka
Hidekazu
H
Sahoo
Akhila K
AK
Yada
Akira
A
Hiyama
Tamejiro
T