Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 17547-17551 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 22 |
| Issue number | 49 |
| DOIs | |
| Publication status | Published - Jan 1 2016 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Chemistry(all)
Cite this
Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane. / Yamamoto, Eiji; Izumi, Kiyotaka; Shishido, Ryosuke; Seki, Tomohiro; Tokodai, Noriaki; Ito, Hajime.
In: Chemistry - A European Journal, Vol. 22, No. 49, 01.01.2016, p. 17547-17551.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane
AU - Yamamoto, Eiji
AU - Izumi, Kiyotaka
AU - Shishido, Ryosuke
AU - Seki, Tomohiro
AU - Tokodai, Noriaki
AU - Ito, Hajime
PY - 2016/1/1
Y1 - 2016/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84996602510&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84996602510&partnerID=8YFLogxK
U2 - 10.1002/chem.201604021
DO - 10.1002/chem.201604021
M3 - Article
AN - SCOPUS:84996602510
VL - 22
SP - 17547
EP - 17551
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 49
ER -