Atropisomeric Carboxylic Acids Synthesis via Nickel-Catalyzed Enantioconvergent Carboxylation of Aza-Biaryl Triflates with CO2
© 2024 Wiley‐VCH GmbH..
Upgrading CO2 to value-added chiral molecules via catalytic asymmetric C-C bond formation is a highly important yet challenging task. Although great progress on the formation of centrally chiral carboxylic acids has been achieved, catalytic construction of axially chiral carboxylic acids with CO2 has never been reported to date. Herein, we report the first catalytic asymmetric synthesis of axially chiral carboxylic acids with CO2, which is enabled by nickel-catalyzed dynamic kinetic asymmetric reductive carboxylation of racemic aza-biaryl triflates. A variety of important axially chiral carboxylic acids, which are valuable but difficult to obtain via catalysis, are generated in an enantioconvergent version. This new methodology features good functional group tolerance, easy to scale-up, facile transformation and avoids cumbersome steps, handling organometallic reagents and using stoichiometric chiral materials. Mechanistic investigations indicate a dynamic kinetic asymmetric transformation process induced by chiral nickel catalysis.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2024 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - (2024) vom: 25. März, Seite e202403401 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Chen, Xiao-Wang [VerfasserIn] |
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| Links: |
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| Themen: |
Asymmetric synthesis |
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| Anmerkungen: |
Date Revised 16.04.2024 published: Print-Electronic Citation Status Publisher |
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| doi: |
10.1002/anie.202403401 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM37017514X |
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| 245 | 1 | 0 | |a Atropisomeric Carboxylic Acids Synthesis via Nickel-Catalyzed Enantioconvergent Carboxylation of Aza-Biaryl Triflates with CO2 |
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| 520 | |a © 2024 Wiley‐VCH GmbH. | ||
| 520 | |a Upgrading CO2 to value-added chiral molecules via catalytic asymmetric C-C bond formation is a highly important yet challenging task. Although great progress on the formation of centrally chiral carboxylic acids has been achieved, catalytic construction of axially chiral carboxylic acids with CO2 has never been reported to date. Herein, we report the first catalytic asymmetric synthesis of axially chiral carboxylic acids with CO2, which is enabled by nickel-catalyzed dynamic kinetic asymmetric reductive carboxylation of racemic aza-biaryl triflates. A variety of important axially chiral carboxylic acids, which are valuable but difficult to obtain via catalysis, are generated in an enantioconvergent version. This new methodology features good functional group tolerance, easy to scale-up, facile transformation and avoids cumbersome steps, handling organometallic reagents and using stoichiometric chiral materials. Mechanistic investigations indicate a dynamic kinetic asymmetric transformation process induced by chiral nickel catalysis | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Asymmetric synthesis | |
| 650 | 4 | |a Axial chirality | |
| 650 | 4 | |a Carbon dioxide | |
| 650 | 4 | |a Enantioconvergent carboxylation | |
| 650 | 4 | |a Nickel | |
| 700 | 1 | |a Li, Chao |e verfasserin |4 aut | |
| 700 | 1 | |a Gui, Yong-Yuan |e verfasserin |4 aut | |
| 700 | 1 | |a Yue, Jun-Ping |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Qi |e verfasserin |4 aut | |
| 700 | 1 | |a Liao, Li-Li |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Jing-Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Ye, Jian-Heng |e verfasserin |4 aut | |
| 700 | 1 | |a Yu, Da-Gang |e verfasserin |4 aut | |
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