Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

A concise and efficient photocatalytic C–C coupling of 1-benzyl-3-cyano-1, 4-dihydropyridine for synthesis of 1,1′-dibenzyl-3, 3′-dicyano-1,1′,4,4′-tetrahydro-4, 4′-bipyridine is described. The reporter system provides a novel technique that facilitates synthesis of C–C coupling derivatives without...

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Autores principales: Chen, Shijun, Zhong, Qidi, Zhu, Hao, Liu, Chunyan, Zhuang, Pengyu, Sun, Wuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978658/
https://www.ncbi.nlm.nih.gov/pubmed/32010676
http://dx.doi.org/10.3389/fchem.2019.00940
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author Chen, Shijun
Zhong, Qidi
Zhu, Hao
Liu, Chunyan
Zhuang, Pengyu
Sun, Wuji
author_facet Chen, Shijun
Zhong, Qidi
Zhu, Hao
Liu, Chunyan
Zhuang, Pengyu
Sun, Wuji
author_sort Chen, Shijun
collection PubMed
description A concise and efficient photocatalytic C–C coupling of 1-benzyl-3-cyano-1, 4-dihydropyridine for synthesis of 1,1′-dibenzyl-3, 3′-dicyano-1,1′,4,4′-tetrahydro-4, 4′-bipyridine is described. The reporter system provides a novel technique that facilitates synthesis of C–C coupling derivatives without addition of transition metals and oxidants or other additives. A plausible synthetic pathway is proposed, and the coupling product was characterized via nuclear magnetic resonance spectroscopy ((1)H and (13)C NMR), high-resolution electrospray ionization mass spectrometry (ESI-HRMS) and X-ray analyses.
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spelling pubmed-69786582020-02-01 Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines Chen, Shijun Zhong, Qidi Zhu, Hao Liu, Chunyan Zhuang, Pengyu Sun, Wuji Front Chem Chemistry A concise and efficient photocatalytic C–C coupling of 1-benzyl-3-cyano-1, 4-dihydropyridine for synthesis of 1,1′-dibenzyl-3, 3′-dicyano-1,1′,4,4′-tetrahydro-4, 4′-bipyridine is described. The reporter system provides a novel technique that facilitates synthesis of C–C coupling derivatives without addition of transition metals and oxidants or other additives. A plausible synthetic pathway is proposed, and the coupling product was characterized via nuclear magnetic resonance spectroscopy ((1)H and (13)C NMR), high-resolution electrospray ionization mass spectrometry (ESI-HRMS) and X-ray analyses. Frontiers Media S.A. 2020-01-17 /pmc/articles/PMC6978658/ /pubmed/32010676 http://dx.doi.org/10.3389/fchem.2019.00940 Text en Copyright © 2020 Chen, Zhong, Zhu, Liu, Zhuang and Sun. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Chen, Shijun
Zhong, Qidi
Zhu, Hao
Liu, Chunyan
Zhuang, Pengyu
Sun, Wuji
Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title_full Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title_fullStr Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title_full_unstemmed Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title_short Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines
title_sort visible-light-induced c–c coupling reaction to synthesize bipyridine from 3-cyano-1,4-dihydropyridines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978658/
https://www.ncbi.nlm.nih.gov/pubmed/32010676
http://dx.doi.org/10.3389/fchem.2019.00940
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