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

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Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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