Visible-Light-Induced Oxidative α-keto-Dichlorination of Arylalkynes by CuCl2 at Room Temperature
© 2022 Wiley-VCH GmbH..
A visible light-induced oxidative α-keto-dichlorination of terminal and internal aryl alkynes was developed to form dichloroacetophenones (DCAPs) and dichlorophenyl-acetophenones (DCPAPs), respectively, by using CuCl2 as a photoredox catalyst in the presence of air at room temperature (without using any exogenous photocatalyst). Here, photoexcited CuCl2 underwent ligand-to-metal charge transfer to generate a Cl radical, which readily added to the alkynes to form DCAPs or DCPAPs in the presence of O2 . This α-keto-dichlorination reaction is a green and mild protocol as it produced water as the only by-product. Moreover, the evaluation of green chemistry metrics indicated that the E-factor (mass of wastes/mass of products) of the current α-keto-chlorination method is around 10.1 times lower than that of a literature-reported photochemical method. The Eco Scale value (score 55, which on a scale of 0-100 indicates an acceptable synthesis) signifies that this process is simple, highly efficient, eco-friendly, and cost-effective.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:15 |
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| Enthalten in: |
ChemSusChem - 15(2022), 17 vom: 07. Sept., Seite e202200957 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Pramod Charpe, Vaibhav [VerfasserIn] |
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| Links: |
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| Themen: |
Alkynes |
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| Anmerkungen: |
Date Completed 09.09.2022 Date Revised 09.09.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/cssc.202200957 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM342512722 |
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| 520 | |a © 2022 Wiley-VCH GmbH. | ||
| 520 | |a A visible light-induced oxidative α-keto-dichlorination of terminal and internal aryl alkynes was developed to form dichloroacetophenones (DCAPs) and dichlorophenyl-acetophenones (DCPAPs), respectively, by using CuCl2 as a photoredox catalyst in the presence of air at room temperature (without using any exogenous photocatalyst). Here, photoexcited CuCl2 underwent ligand-to-metal charge transfer to generate a Cl radical, which readily added to the alkynes to form DCAPs or DCPAPs in the presence of O2 . This α-keto-dichlorination reaction is a green and mild protocol as it produced water as the only by-product. Moreover, the evaluation of green chemistry metrics indicated that the E-factor (mass of wastes/mass of products) of the current α-keto-chlorination method is around 10.1 times lower than that of a literature-reported photochemical method. The Eco Scale value (score 55, which on a scale of 0-100 indicates an acceptable synthesis) signifies that this process is simple, highly efficient, eco-friendly, and cost-effective | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a CuCl2 | |
| 650 | 4 | |a chlorination | |
| 650 | 4 | |a halogenation | |
| 650 | 4 | |a photocatalysis | |
| 650 | 4 | |a sustainable chemistry | |
| 650 | 7 | |a Alkynes |2 NLM | |
| 700 | 1 | |a Gupta, Mahima |e verfasserin |4 aut | |
| 700 | 1 | |a Chu Hwang, Kuo |e verfasserin |4 aut | |
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