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Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex
A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-c...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9214885/ https://www.ncbi.nlm.nih.gov/pubmed/35799801 http://dx.doi.org/10.1039/d2sc01909d |
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author | Pan, Pan Liu, Shihan Lan, Yu Zeng, Huiying Li, Chao-Jun |
author_facet | Pan, Pan Liu, Shihan Lan, Yu Zeng, Huiying Li, Chao-Jun |
author_sort | Pan, Pan |
collection | PubMed |
description | A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed that the association of the hydrazone anion with aryl halides formed an electron donor–acceptor complex, which when excited with visible light generated an aryl radical via single-electron transfer. |
format | Online Article Text |
id | pubmed-9214885 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-92148852022-07-06 Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex Pan, Pan Liu, Shihan Lan, Yu Zeng, Huiying Li, Chao-Jun Chem Sci Chemistry A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed that the association of the hydrazone anion with aryl halides formed an electron donor–acceptor complex, which when excited with visible light generated an aryl radical via single-electron transfer. The Royal Society of Chemistry 2022-05-23 /pmc/articles/PMC9214885/ /pubmed/35799801 http://dx.doi.org/10.1039/d2sc01909d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Pan, Pan Liu, Shihan Lan, Yu Zeng, Huiying Li, Chao-Jun Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title | Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title_full | Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title_fullStr | Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title_full_unstemmed | Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title_short | Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex |
title_sort | visible-light-induced cross-coupling of aryl iodides with hydrazones via an eda-complex |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9214885/ https://www.ncbi.nlm.nih.gov/pubmed/35799801 http://dx.doi.org/10.1039/d2sc01909d |
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