Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination
A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secon...
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| Published in | Organic letters Vol. 23; no. 2; pp. 433 - 437 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Amer Chemical Soc
15.01.2021
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| Abstract | A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important gamma-lactones in one further step. |
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| AbstractList | A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step.A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step. A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step. A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important gamma-lactones in one further step. |
| Author | Kozlowski, Marisa C. Hendrick, Charles E. Basnet, Prakash Hong, Gang |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33393785$$D View this record in MEDLINE/PubMed |
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| Snippet | A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated... |
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| SubjectTerms | alkenes Alkenes - chemistry carbon Catalysis Chemistry Chemistry, Organic chlorides Copper Halogenation Lactones - chemistry Molecular Structure Nitriles - chemistry oxidation Oxidation-Reduction Physical Sciences Science & Technology |
| Title | Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination |
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