Visible-Light-Promoted Aerobic α-Thiocyanation of Carbonyl Compounds with Ammonium Thiocyanate
In the present study, we successfully developed an efficient thiocyanation of carbonyl compounds by using low-toxicity and inexpensive ammonium thiocyanate as the thiocyanate source under visible light in air (O2) at room temperature. This unified strategy is very facile for thiocyanation of various carbonyl compound derivatives (β-keto esters, β-keto amides, pyrazo-5-ones, isoxazol-5-ones, etc.). More importantly, the reaction proceeded smoothly without the addition of a photocatalyst and strong oxidant, ultimately minimizing the production of chemical waste. Furthermore, this green and sustainable synthetic chemistry can be used in the late-stage functionalization (LSF) of biorelevant compounds, which offers unique opportunities to achieve smooth and clean thiocyanation of drugs under mild reaction conditions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:89 |
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| Enthalten in: |
The Journal of organic chemistry - 89(2024), 5 vom: 01. März, Seite 3453-3470 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wang, Yakun [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 01.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.3c02896 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM368249565 |
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| 520 | |a In the present study, we successfully developed an efficient thiocyanation of carbonyl compounds by using low-toxicity and inexpensive ammonium thiocyanate as the thiocyanate source under visible light in air (O2) at room temperature. This unified strategy is very facile for thiocyanation of various carbonyl compound derivatives (β-keto esters, β-keto amides, pyrazo-5-ones, isoxazol-5-ones, etc.). More importantly, the reaction proceeded smoothly without the addition of a photocatalyst and strong oxidant, ultimately minimizing the production of chemical waste. Furthermore, this green and sustainable synthetic chemistry can be used in the late-stage functionalization (LSF) of biorelevant compounds, which offers unique opportunities to achieve smooth and clean thiocyanation of drugs under mild reaction conditions | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Liu, Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yingying |e verfasserin |4 aut | |
| 700 | 1 | |a Du, Xiaoyu |e verfasserin |4 aut | |
| 700 | 1 | |a Song, Haojie |e verfasserin |4 aut | |
| 700 | 1 | |a Fang, Lizhen |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Liqiang |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Tao |e verfasserin |4 aut | |
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