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 journalArticle

2 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 languageEnglish
Pages (from-to)17547-17551
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number49
DOIs
Publication statusPublished - Jan 1 2016

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Bearings (structural)
Boranes
Alkali Metals
Iodides
Alkali metals
Bromides
Substitution reactions
diphenyl

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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, 01.01.2016, p. 17547-17551.

Research output: Contribution to journalArticle

Yamamoto, Eiji ; Izumi, Kiyotaka ; Shishido, Ryosuke ; Seki, Tomohiro ; Tokodai, Noriaki ; Ito, Hajime. / Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 49. pp. 17547-17551.
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