Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane.
The first dimesitylboryl substitution of aryl halides with a silylborane bearing a dimesitylboryl group in the presence of alkali-metal alkoxides is described. The reactions of aryl bromides or iodides with Ph2MeSi-BMes2and Na(OtBu) afforded the desired aryl dimesitylboranes in good to high yields and with high borylation/silylation ratios. Selective reaction of the sterically less-hindered C-Br bond of dibromoarenes provided monoborylated products. This reaction was used to rapidly construct a D-π-A aryl dimesityl borane with a non-symmetrical biphenyl spacer.
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Eiji
E
Yamamoto
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Kiyotaka
K
Izumi
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Ryosuke
R
Shishido
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Tomohiro
T
Seki
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Noriaki
N
Tokodai
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
Hajime
http://orcid.org/0000-0003-3852-6721
H
Ito
base-mediated borylation; boryl substitution; dimesitylborylation; silylborane; triaryl borane