4.8 Article

Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes

Journal

CHEMICAL SCIENCE
Volume 8, Issue 11, Pages 7537-7544

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc02294h

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Funding

  1. National Natural Science Foundation of China [21272198]
  2. Hong Kong Research Grants Council [PolyU 153031/14P, 153001/17P, PolyU11/CRF/13E]
  3. State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology

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A new photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization reaction is developed. The reaction was chemoselective towards silyl-substituted alkynes with excellent regioselectivity and good functional group compatibility, giving a series of silyl-substituted quinolizinium derivatives as products. The newly synthesized fluorescent quinolizinium compounds, named JR-Fluor-1, possessed tunable emission properties and large Stokes shifts. With unique photophysical properties, the fluorophores have been applied in photooxidative amidations as efficient photocatalysts and cellular imaging with switchable subcellular localization properties.

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