Direct Introduction of a Dimesitylboryl Group Using Base‐Mediated Substitution of Aryl Halides with Silyldimesitylborane |
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Authors: | Dr Eiji Yamamoto Kiyotaka Izumi Ryosuke Shishido Prof?Dr Tomohiro Seki Noriaki Tokodai Prof?Dr Hajime Ito |
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Institution: | Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, Japan |
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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?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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Keywords: | base-mediated borylation boryl substitution dimesitylborylation silylborane triaryl borane |
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