Journal Article 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

22 ( 49 )  , pp.17547 - 17551 , 2016-12-05 , Wiley-Blackwell
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-BMes(2) 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-pi-A aryl dimesityl borane with a non-symmetrical biphenyl spacer.

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