Deconstructive Carboxylation of Activated Alkenes with Carbon Dioxide
© 2023 Wiley-VCH GmbH..
Carboxylation with carbon dioxide (CO2 ) represents one notable methodology to produce carboxylic acids. In contrast to carbon-heteroatom bonds, carbon-carbon bond cleavage for carboxylation with CO2 is far more challenging due to their inherent and less favorable orbital directionality for interacting with transition metals. Here we report a photocatalytic protocol for the deconstructive carboxylation of alkenes with CO2 to generate carboxylic acids in the absence of transition metals. It is emphasized that our protocol provides carboxylic acids with obviously unchanged carbon numbers when terminal alkenes were used. To show the power of this strategy, a variety of pharmaceutically relevant applications including the modular synthesis of propionate nonsteroidal anti-inflammatory drugs and the late-stage carboxylation of bioactive molecule derivatives are demonstrated.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:63 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 63(2024), 5 vom: 25. Jan., Seite e202313030 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yuan, Pan-Feng [VerfasserIn] |
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| Links: |
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| Themen: |
Alkenes |
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| Anmerkungen: |
Date Revised 18.01.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202313030 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a Carboxylation with carbon dioxide (CO2 ) represents one notable methodology to produce carboxylic acids. In contrast to carbon-heteroatom bonds, carbon-carbon bond cleavage for carboxylation with CO2 is far more challenging due to their inherent and less favorable orbital directionality for interacting with transition metals. Here we report a photocatalytic protocol for the deconstructive carboxylation of alkenes with CO2 to generate carboxylic acids in the absence of transition metals. It is emphasized that our protocol provides carboxylic acids with obviously unchanged carbon numbers when terminal alkenes were used. To show the power of this strategy, a variety of pharmaceutically relevant applications including the modular synthesis of propionate nonsteroidal anti-inflammatory drugs and the late-stage carboxylation of bioactive molecule derivatives are demonstrated | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Alkenes | |
| 650 | 4 | |a Carbon Dioxide | |
| 650 | 4 | |a Carboxylation | |
| 650 | 4 | |a Photocatalysis | |
| 650 | 4 | |a Synthetic Methods | |
| 700 | 1 | |a Yang, Zhao |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Shan-Shan |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Can-Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Xiu-Long |e verfasserin |4 aut | |
| 700 | 1 | |a Meng, Qing-Yuan |e verfasserin |4 aut | |
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