Fused heteroaromatic dihydrosiloles: Synthesis and double-fold modification

Alexey Kuznetsov, Yoshiharu Onishi, Yoshihiro Inamoto, Vladimir Gevorgyan

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionalized heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

Original languageEnglish (US)
Pages (from-to)2498-2501
Number of pages4
JournalOrganic Letters
Volume15
Issue number10
DOIs
StatePublished - May 17 2013
Externally publishedYes

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Hydrosilylation
Regioselectivity
synthesis
Functional groups
Electrons
catalysts
Catalysts
electrons

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Fused heteroaromatic dihydrosiloles : Synthesis and double-fold modification. / Kuznetsov, Alexey; Onishi, Yoshiharu; Inamoto, Yoshihiro; Gevorgyan, Vladimir.

In: Organic Letters, Vol. 15, No. 10, 17.05.2013, p. 2498-2501.

Research output: Contribution to journalArticle

Kuznetsov, Alexey ; Onishi, Yoshiharu ; Inamoto, Yoshihiro ; Gevorgyan, Vladimir. / Fused heteroaromatic dihydrosiloles : Synthesis and double-fold modification. In: Organic Letters. 2013 ; Vol. 15, No. 10. pp. 2498-2501.
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