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NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study

A facile and general approach was developed for the efficient construction of functionalized bromoquinolines by the dehydrogenation of tetrahydroquinolines using NBS as the electrophile and as oxidant. The cascade transformation proceeded with good functional group tolerance under metal-free conditi...

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Autores principales: Yang, Ruchun, Xiong, Yongge, Deng, Si, Bai, Jiang, Song, Xian-Rong, Xiao, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10646511/
https://www.ncbi.nlm.nih.gov/pubmed/38025860
http://dx.doi.org/10.1039/d3ra06747e
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author Yang, Ruchun
Xiong, Yongge
Deng, Si
Bai, Jiang
Song, Xian-Rong
Xiao, Qiang
author_facet Yang, Ruchun
Xiong, Yongge
Deng, Si
Bai, Jiang
Song, Xian-Rong
Xiao, Qiang
author_sort Yang, Ruchun
collection PubMed
description A facile and general approach was developed for the efficient construction of functionalized bromoquinolines by the dehydrogenation of tetrahydroquinolines using NBS as the electrophile and as oxidant. The cascade transformation proceeded with good functional group tolerance under metal-free conditions with a short reaction duration. Various tetrahydroquinolines bearing either electron-rich or electron-deficient groups at different positions were successfully converted into the corresponding target products in moderate to high yields under mild conditions. It is worth noting that the obtained polybromoquinolines could further undergo classic metal-catalyzed cross-coupling reactions with good regioselectivity. The Sonagashira coupling reaction occurred regioselectively in the C-6 position of the obtained products followed by a Suzuki coupling reaction to give multifunctionalized quinolines. The mechanism indicated that electrophilic bromination/radical dehydrogenation sequences occurred in one pot.
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spelling pubmed-106465112023-11-15 NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study Yang, Ruchun Xiong, Yongge Deng, Si Bai, Jiang Song, Xian-Rong Xiao, Qiang RSC Adv Chemistry A facile and general approach was developed for the efficient construction of functionalized bromoquinolines by the dehydrogenation of tetrahydroquinolines using NBS as the electrophile and as oxidant. The cascade transformation proceeded with good functional group tolerance under metal-free conditions with a short reaction duration. Various tetrahydroquinolines bearing either electron-rich or electron-deficient groups at different positions were successfully converted into the corresponding target products in moderate to high yields under mild conditions. It is worth noting that the obtained polybromoquinolines could further undergo classic metal-catalyzed cross-coupling reactions with good regioselectivity. The Sonagashira coupling reaction occurred regioselectively in the C-6 position of the obtained products followed by a Suzuki coupling reaction to give multifunctionalized quinolines. The mechanism indicated that electrophilic bromination/radical dehydrogenation sequences occurred in one pot. The Royal Society of Chemistry 2023-11-15 /pmc/articles/PMC10646511/ /pubmed/38025860 http://dx.doi.org/10.1039/d3ra06747e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Ruchun
Xiong, Yongge
Deng, Si
Bai, Jiang
Song, Xian-Rong
Xiao, Qiang
NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title_full NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title_fullStr NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title_full_unstemmed NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title_short NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
title_sort nbs-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10646511/
https://www.ncbi.nlm.nih.gov/pubmed/38025860
http://dx.doi.org/10.1039/d3ra06747e
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