Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems

Eiji Yamamoto, Kiyotaka Izumi, Yuko Horita, Hajime Ito

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.

Original languageEnglish
Pages (from-to)19997-20000
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number49
DOIs
Publication statusPublished - Dec 12 2012
Externally publishedYes

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Bromides
Transition metals
Substitution reactions
Metals
Functional groups
Contamination
Substrates
alkoxyl radical

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Anomalous reactivity of silylborane : Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems. / Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ito, Hajime.

In: Journal of the American Chemical Society, Vol. 134, No. 49, 12.12.2012, p. 19997-20000.

Research output: Contribution to journalArticle

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