Copper-Catalyzed Asymmetric Cyanation of Propargylic Radicals via Direct Decarboxylation of Propargylic Carboxylic Acids
Chiral propargylic cyanides are often used as small-molecule feedstocks for the introduction of chiral centers into various valuable products and complex molecules. Here, we have developed a highly atom-economical strategy for the chiral copper complex-catalyzed synthesis of chiral propargylic cyanides. Propargylic radicals can be smoothly obtained by direct decarboxylation of the propargylic carboxylic acids without preactivation. The reactions show excellent selectivity and functional group compatibility. Gram-scale reaction and several conversion reactions from chiral propargylic cyanide have demonstrated the synthetic value of this strategy.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:25 |
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| Enthalten in: |
Organic letters - 25(2023), 27 vom: 14. Juli, Seite 5006-5010 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Guang'an [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 17.07.2023 Date Revised 18.07.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.3c01637 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM358858429 |
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| 245 | 1 | 0 | |a Copper-Catalyzed Asymmetric Cyanation of Propargylic Radicals via Direct Decarboxylation of Propargylic Carboxylic Acids |
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| 500 | |a Date Revised 18.07.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Chiral propargylic cyanides are often used as small-molecule feedstocks for the introduction of chiral centers into various valuable products and complex molecules. Here, we have developed a highly atom-economical strategy for the chiral copper complex-catalyzed synthesis of chiral propargylic cyanides. Propargylic radicals can be smoothly obtained by direct decarboxylation of the propargylic carboxylic acids without preactivation. The reactions show excellent selectivity and functional group compatibility. Gram-scale reaction and several conversion reactions from chiral propargylic cyanide have demonstrated the synthetic value of this strategy | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Carboxylic Acids |2 NLM | |
| 650 | 7 | |a Copper |2 NLM | |
| 650 | 7 | |a 789U1901C5 |2 NLM | |
| 650 | 7 | |a Cyanides |2 NLM | |
| 700 | 1 | |a Pei, Yonghong |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Junwei |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Xinyu |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Zhongxian |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Fengqian |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Junliang |e verfasserin |4 aut | |
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