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

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 quinoliziniu...

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Autores principales: Deng, Jie-Ren, Chan, Wing-Cheung, Chun-Him Lai, Nathanael, Yang, Bin, Tsang, Chui-Shan, Chi-Bun Ko, Ben, Lai-Fung Chan, Sharon, Wong, Man-Kin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5676248/
https://www.ncbi.nlm.nih.gov/pubmed/29163908
http://dx.doi.org/10.1039/c7sc02294h
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author Deng, Jie-Ren
Chan, Wing-Cheung
Chun-Him Lai, Nathanael
Yang, Bin
Tsang, Chui-Shan
Chi-Bun Ko, Ben
Lai-Fung Chan, Sharon
Wong, Man-Kin
author_facet Deng, Jie-Ren
Chan, Wing-Cheung
Chun-Him Lai, Nathanael
Yang, Bin
Tsang, Chui-Shan
Chi-Bun Ko, Ben
Lai-Fung Chan, Sharon
Wong, Man-Kin
author_sort Deng, Jie-Ren
collection PubMed
description 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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spelling pubmed-56762482017-11-21 Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes Deng, Jie-Ren Chan, Wing-Cheung Chun-Him Lai, Nathanael Yang, Bin Tsang, Chui-Shan Chi-Bun Ko, Ben Lai-Fung Chan, Sharon Wong, Man-Kin Chem Sci Chemistry 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. Royal Society of Chemistry 2017-11-01 2017-09-04 /pmc/articles/PMC5676248/ /pubmed/29163908 http://dx.doi.org/10.1039/c7sc02294h Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Deng, Jie-Ren
Chan, Wing-Cheung
Chun-Him Lai, Nathanael
Yang, Bin
Tsang, Chui-Shan
Chi-Bun Ko, Ben
Lai-Fung Chan, Sharon
Wong, Man-Kin
Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title_full Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title_fullStr Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title_full_unstemmed Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title_short Photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
title_sort photosensitizer-free visible light-mediated gold-catalysed cis-difunctionalization of silyl-substituted alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5676248/
https://www.ncbi.nlm.nih.gov/pubmed/29163908
http://dx.doi.org/10.1039/c7sc02294h
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