Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to C(α)-arylate amides (α to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was...

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Autores principales: Zhang, Yongqiang, Teuscher, Kevin B., Ji, Haitao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5968545/
https://www.ncbi.nlm.nih.gov/pubmed/29899938
http://dx.doi.org/10.1039/c5sc03640b
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author Zhang, Yongqiang
Teuscher, Kevin B.
Ji, Haitao
author_facet Zhang, Yongqiang
Teuscher, Kevin B.
Ji, Haitao
author_sort Zhang, Yongqiang
collection PubMed
description A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to C(α)-arylate amides (α to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new C(sp(2))–C(sp(2)) and C(sp(3))–C(sp(2)) bonds and access to important pharmacophores of broad utility using commercially available reagents.
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spelling pubmed-59685452018-06-13 Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction Zhang, Yongqiang Teuscher, Kevin B. Ji, Haitao Chem Sci Chemistry A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to C(α)-arylate amides (α to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new C(sp(2))–C(sp(2)) and C(sp(3))–C(sp(2)) bonds and access to important pharmacophores of broad utility using commercially available reagents. Royal Society of Chemistry 2016-03-01 2015-12-07 /pmc/articles/PMC5968545/ /pubmed/29899938 http://dx.doi.org/10.1039/c5sc03640b Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Zhang, Yongqiang
Teuscher, Kevin B.
Ji, Haitao
Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title_full Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title_fullStr Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title_full_unstemmed Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title_short Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
title_sort direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5968545/
https://www.ncbi.nlm.nih.gov/pubmed/29899938
http://dx.doi.org/10.1039/c5sc03640b
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AT jihaitao directaheteroarylationofamidesatonitrogenandethersthroughabenzaldehydemediatedphotoredoxreaction

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