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Updated: Mar 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with
Eiji Yamamoto1, Kiyotaka Izumi1, Ryosuke Shishido1
1Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
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 Ph2 MeSi-BMes2 and 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.
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