Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones
Abstract Herein, the study reports the first electrochemical nickel‐catalyzed enantioselective hydro‐arylation/alkenylation of enones in an undivided cell with low‐cost electrodes in the absence of external reductants and supporting electrolytes. Aryl bromides/iodides/triflates or alkenyl bromides a...
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| Format: | Article |
| Language: | English |
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Wiley
2024-11-01
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| Series: | Advanced Science |
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| Online Access: | https://doi.org/10.1002/advs.202405926 |
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| author | Zenghui Ye Weiyuan Ma Xi Zhang Huaqing Liu Fengzhi Zhang |
| author_facet | Zenghui Ye Weiyuan Ma Xi Zhang Huaqing Liu Fengzhi Zhang |
| author_sort | Zenghui Ye |
| collection | DOAJ |
| description | Abstract Herein, the study reports the first electrochemical nickel‐catalyzed enantioselective hydro‐arylation/alkenylation of enones in an undivided cell with low‐cost electrodes in the absence of external reductants and supporting electrolytes. Aryl bromides/iodides/triflates or alkenyl bromides are employed as electrophiles for the efficient preparation of more than 56 valuable β‐arylated/alkenylated ketones in a simple manner (up to 97% yield, 97% ee). With the advantages of electrochemistry, excellent functional group tolerance and late‐stage modification of complex natural products and pharmaceuticals made the established protocol greener and more economic. Mechanism investigation suggests that a NiI/NiIII cycle may be involved in this electro‐reductive reaction rather than metal reductant driven Ni0/NiII cycle. Overall, the efficient electrochemical activation and turnover of the nickel catalyst avoid the drawbacks posed by the employment of stoichiometric amount of sensitive metal powder reductants. |
| format | Article |
| id | doaj-art-dbe3ccf4308347418d30f4056a8ef9e8 |
| institution | DOAJ |
| issn | 2198-3844 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Wiley |
| record_format | Article |
| series | Advanced Science |
| spelling | doaj-art-dbe3ccf4308347418d30f4056a8ef9e82025-08-20T02:58:41ZengWileyAdvanced Science2198-38442024-11-011142n/an/a10.1002/advs.202405926Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of EnonesZenghui Ye0Weiyuan Ma1Xi Zhang2Huaqing Liu3Fengzhi Zhang4School of Pharmacy Hangzhou Medical College Hangzhou Zhejiang 311399 ChinaSchool of Pharmacy Hangzhou Medical College Hangzhou Zhejiang 311399 ChinaSchool of Pharmacy Hangzhou Medical College Hangzhou Zhejiang 311399 ChinaSchool of Pharmacy Hangzhou Medical College Hangzhou Zhejiang 311399 ChinaSchool of Pharmacy Hangzhou Medical College Hangzhou Zhejiang 311399 ChinaAbstract Herein, the study reports the first electrochemical nickel‐catalyzed enantioselective hydro‐arylation/alkenylation of enones in an undivided cell with low‐cost electrodes in the absence of external reductants and supporting electrolytes. Aryl bromides/iodides/triflates or alkenyl bromides are employed as electrophiles for the efficient preparation of more than 56 valuable β‐arylated/alkenylated ketones in a simple manner (up to 97% yield, 97% ee). With the advantages of electrochemistry, excellent functional group tolerance and late‐stage modification of complex natural products and pharmaceuticals made the established protocol greener and more economic. Mechanism investigation suggests that a NiI/NiIII cycle may be involved in this electro‐reductive reaction rather than metal reductant driven Ni0/NiII cycle. Overall, the efficient electrochemical activation and turnover of the nickel catalyst avoid the drawbacks posed by the employment of stoichiometric amount of sensitive metal powder reductants.https://doi.org/10.1002/advs.202405926asymmetric synthesischiral nickel catalystselectrochemical reductive conjugate arylationelectrochemistry |
| spellingShingle | Zenghui Ye Weiyuan Ma Xi Zhang Huaqing Liu Fengzhi Zhang Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones Advanced Science asymmetric synthesis chiral nickel catalysts electrochemical reductive conjugate arylation electrochemistry |
| title | Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones |
| title_full | Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones |
| title_fullStr | Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones |
| title_full_unstemmed | Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones |
| title_short | Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones |
| title_sort | electrochemically driven nickel catalyzed enantioselective hydro arylation alkenylation of enones |
| topic | asymmetric synthesis chiral nickel catalysts electrochemical reductive conjugate arylation electrochemistry |
| url | https://doi.org/10.1002/advs.202405926 |
| work_keys_str_mv | AT zenghuiye electrochemicallydrivennickelcatalyzedenantioselectivehydroarylationalkenylationofenones AT weiyuanma electrochemicallydrivennickelcatalyzedenantioselectivehydroarylationalkenylationofenones AT xizhang electrochemicallydrivennickelcatalyzedenantioselectivehydroarylationalkenylationofenones AT huaqingliu electrochemicallydrivennickelcatalyzedenantioselectivehydroarylationalkenylationofenones AT fengzhizhang electrochemicallydrivennickelcatalyzedenantioselectivehydroarylationalkenylationofenones |