Rhodium-catalyzed enantioselective synthesis and properties of silicon-stereogenic benzofuranylmethylidene-benzoxasiloles

Tomoya Namba, Yu Shibata, Haruki Sugiyama, Kota Teraoka, Hidehiro Uekusa, Ken Tanaka

Research output: Contribution to journalArticle

Abstract

The enantioselective synthesis of silicon-stereogenic benzo-furanylmethylidene-benzoxasiloles was achieved with moderate enantioselectivity by the cationic rhodium(I)/(S)-BINAP complex-catalyzed desymmetrization of symmetrical bis(2-ethynyl-phenol)silanes, possessing the tert-butyl and methyl groups on the silicon atom. This reaction involves 1,2-silicon/1,3-carbon migrations and oxycyclization, and the 1,2-silicon migration constructs the stereogenic silicon center. The thus obtained benzofuranylmethylidene-benzoxasiloles with the electron-donating methoxy, methyl, and phenyl groups on two benzene rings showed good fluorescence quantum yields in solution state, on the other hand, that with the electron-withdrawing trifluoromethyl groups on two benzene rings showed good fluorescence quantum yield in solid state.

Original languageEnglish
Pages (from-to)787-790
Number of pages4
JournalChemistry Letters
Volume47
Issue number6
DOIs
Publication statusPublished - 2018 Jan 1
Externally publishedYes

Fingerprint

Rhodium
Silicon
Quantum yield
Benzene
Fluorescence
Silanes
Electrons
Enantioselectivity
Phenol
Carbon
Atoms

Keywords

  • Fluorescent chiral organosilicon
  • Rhodium catalysis
  • Silicon-stereogenic compounds

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rhodium-catalyzed enantioselective synthesis and properties of silicon-stereogenic benzofuranylmethylidene-benzoxasiloles. / Namba, Tomoya; Shibata, Yu; Sugiyama, Haruki; Teraoka, Kota; Uekusa, Hidehiro; Tanaka, Ken.

In: Chemistry Letters, Vol. 47, No. 6, 01.01.2018, p. 787-790.

Research output: Contribution to journalArticle

Namba, Tomoya ; Shibata, Yu ; Sugiyama, Haruki ; Teraoka, Kota ; Uekusa, Hidehiro ; Tanaka, Ken. / Rhodium-catalyzed enantioselective synthesis and properties of silicon-stereogenic benzofuranylmethylidene-benzoxasiloles. In: Chemistry Letters. 2018 ; Vol. 47, No. 6. pp. 787-790.
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AU - Sugiyama, Haruki

AU - Teraoka, Kota

AU - Uekusa, Hidehiro

AU - Tanaka, Ken

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