1. Rhodium-catalyzed enantioselective synthesis and properties of silicon-stereogenic benzofuranylmethylidene-benzoxasiloles
- Author
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Namba, Tomoya, Shibata, Yu, Sugiyama, Haruki, Teraoka, Kota, UEKUSA, hidehiro, and Tanaka, Ken.
- Subjects
fluorescence benzofuranylmethylidene benzoxasilole ,Silanes ,Trifluoromethyl ,010405 organic chemistry ,Cationic polymerization ,Enantioselective synthesis ,chemistry.chemical_element ,Quantum yield ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Desymmetrization ,Medicinal chemistry ,0104 chemical sciences ,Rhodium ,Stereocenter ,chemistry.chemical_compound ,chemistry ,rhodium catalyzed enantioselective benzofuranylmethylidene benzoxasilole prepn crystal mol structure - Abstract
The enantioselective synthesis of silicon-stereogenic benzofuranylmethylidene-benzoxasiloles was achieved with moderate enantioselectivity by the cationic rhodium(I)/(S)-BINAP complex-catalyzed desymmetrization of symmetrical bis(2-ethynylphenol)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.
- Published
- 2018