Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams
Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt cat...
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| Published in | Green chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 5; pp. 1548 - 1552 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
09.03.2020
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H
2
as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained.
Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. |
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| AbstractList | Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained. Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H 2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained. Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H 2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained. Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H-2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained. |
| Author | Lin, Yueping Zeng, Li Bu, Faxiang Weng, Yaqing Cao, Yangmin Yuan, Yong Jiang, Xiaomei Wang, Tangwei Lei, Aiwen |
| AuthorAffiliation | Wuhan University College of Chemistry and Molecular Sciences National Research Center for Carbohydrate Synthesis Jiangxi Normal University Institute for Advanced Studies (IAS) |
| AuthorAffiliation_xml | – name: National Research Center for Carbohydrate Synthesis – name: College of Chemistry and Molecular Sciences – name: Institute for Advanced Studies (IAS) – name: Wuhan University – name: Jiangxi Normal University |
| Author_xml | – sequence: 1 givenname: Yangmin surname: Cao fullname: Cao, Yangmin – sequence: 2 givenname: Yong surname: Yuan fullname: Yuan, Yong – sequence: 3 givenname: Yueping surname: Lin fullname: Lin, Yueping – sequence: 4 givenname: Xiaomei surname: Jiang fullname: Jiang, Xiaomei – sequence: 5 givenname: Yaqing surname: Weng fullname: Weng, Yaqing – sequence: 6 givenname: Tangwei surname: Wang fullname: Wang, Tangwei – sequence: 7 givenname: Faxiang surname: Bu fullname: Bu, Faxiang – sequence: 8 givenname: Li surname: Zeng fullname: Zeng, Li – sequence: 9 givenname: Aiwen surname: Lei fullname: Lei, Aiwen |
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| Keywords | OXIDATIVE CROSS-COUPLING/CYCLIZATION REARRANGEMENT ALKENES OLEFINATION PYRROLIDINES ARYL SULFONAMIDES 1,1-DIOXIDES ALKYNES C-H ACTIVATION ACCESS |
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| Snippet | Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally... |
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| SubjectTerms | Alkynes Anodizing Catalysts Chemical reactions Chemistry Chemistry, Multidisciplinary Cobalt Electrochemistry Green & Sustainable Science & Technology Green chemistry Organic chemistry Oxidants Oxidation Oxidizing agents Physical Sciences Science & Technology Science & Technology - Other Topics Sulfonamides |
| Title | Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams |
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