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

Jie Ren Deng; Wing Cheung Chan; Nathanael Chun-Him Lai; Bin Yang; Chui Shan Tsang; Ben Chi-Bun Ko; Sharon Lai-Fung Chan; Man Kin Wong

doi:10.1039/c7sc02294h

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

Jie Ren Deng, Wing Cheung Chan, Nathanael Chun-Him Lai, Bin Yang, Chui Shan Tsang, Ben Chi-Bun Ko, Sharon Lai-Fung Chan, Man Kin Wong

Research output: Journal article publication › Journal article › Academic research › peer-review

66 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7537-7544
Number of pages	8
Journal	Chemical Science
Volume	8
Issue number	11
DOIs	https://doi.org/10.1039/c7sc02294h
Publication status	Published - 1 Jan 2017

ASJC Scopus subject areas

General Chemistry

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10.1039/c7sc02294h

http://hdl.handle.net/10397/75673

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title = "Photosensitizer-free visible light-mediated gold-catalysed: Cis -difunctionalization of silyl-substituted alkynes",

abstract = "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.",

author = "Deng, {Jie Ren} and Chan, {Wing Cheung} and {Chun-Him Lai}, Nathanael and Bin Yang and Tsang, {Chui Shan} and {Chi-Bun Ko}, Ben and {Lai-Fung Chan}, Sharon and Wong, {Man Kin}",

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AU - Deng, Jie Ren

AU - Chan, Wing Cheung

AU - Chun-Him Lai, Nathanael

AU - Yang, Bin

AU - Tsang, Chui Shan

AU - Chi-Bun Ko, Ben

AU - Lai-Fung Chan, Sharon

AU - Wong, Man Kin

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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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DO - 10.1039/c7sc02294h

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EP - 7544

JO - Chemical Science

JF - Chemical Science

IS - 11

ER -

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

Abstract

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