Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane

Eiji Yamamoto; Kiyotaka Izumi; Ryosuke Shishido; Tomohiro Seki; Noriaki Tokodai; Hajime Ito

doi:10.1002/chem.201604021

Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane

Eiji Yamamoto, Kiyotaka Izumi, Ryosuke Shishido, Tomohiro Seki, Noriaki Tokodai, Hajime Ito

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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	https://doi.org/10.1002/chem.201604021
Publication status	Published - Dec 5 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.201604021

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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, 05.12.2016, p. 17547-17551.

Research output: Contribution to journal › Article › peer-review

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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−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.",

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AU - Yamamoto, Eiji

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AU - Shishido, Ryosuke

AU - Seki, Tomohiro

AU - Tokodai, Noriaki

AU - Ito, Hajime

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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.

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Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane

Abstract

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