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 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
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Cite this
Yamamoto, E., Izumi, K., Shishido, R., Seki, T., Tokodai, N., & Ito, H. (2016). Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane. Chemistry - A European Journal, 22(49), 17547-17551. https://doi.org/10.1002/chem.201604021