Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis
Abstract Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excel...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56377-w |
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| author | Yun-Zhao Wang Bing Sun Jian-Feng Guo Xiao-Yu Zhu Yu-Cheng Gu Ya-Ping Han Cong Ma Tian-Sheng Mei |
| author_facet | Yun-Zhao Wang Bing Sun Jian-Feng Guo Xiao-Yu Zhu Yu-Cheng Gu Ya-Ping Han Cong Ma Tian-Sheng Mei |
| author_sort | Yun-Zhao Wang |
| collection | DOAJ |
| description | Abstract Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity. This catalytic reaction can not only be applied to aryl chlorides/bromides, which are challenging to access by other means, but also to benzyl chlorides containing silicon groups. Additionally, the absence of a sacrificial anode lays a foundation for scalability. The combination of cyclic voltammetry analysis with electrode potential studies suggests that NiI species activate aryl halides via oxidative addition and alkyl chlorides via single electron transfer. |
| format | Article |
| id | doaj-art-1c3e6cadfbcd427ab3a20f0fad8f8b60 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-1c3e6cadfbcd427ab3a20f0fad8f8b602025-02-02T12:33:10ZengNature PortfolioNature Communications2041-17232025-01-011611810.1038/s41467-025-56377-wEnantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysisYun-Zhao Wang0Bing Sun1Jian-Feng Guo2Xiao-Yu Zhu3Yu-Cheng Gu4Ya-Ping Han5Cong Ma6Tian-Sheng Mei7State Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesSyngenta, Jealott’s Hill International Research CentreSchool of Chemical Engineering and Technology, Hebei University of TechnologyState Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesAbstract Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity. This catalytic reaction can not only be applied to aryl chlorides/bromides, which are challenging to access by other means, but also to benzyl chlorides containing silicon groups. Additionally, the absence of a sacrificial anode lays a foundation for scalability. The combination of cyclic voltammetry analysis with electrode potential studies suggests that NiI species activate aryl halides via oxidative addition and alkyl chlorides via single electron transfer.https://doi.org/10.1038/s41467-025-56377-w |
| spellingShingle | Yun-Zhao Wang Bing Sun Jian-Feng Guo Xiao-Yu Zhu Yu-Cheng Gu Ya-Ping Han Cong Ma Tian-Sheng Mei Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis Nature Communications |
| title | Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis |
| title_full | Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis |
| title_fullStr | Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis |
| title_full_unstemmed | Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis |
| title_short | Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis |
| title_sort | enantioselective reductive cross couplings to forge c sp2 c sp3 bonds by merging electrochemistry with nickel catalysis |
| url | https://doi.org/10.1038/s41467-025-56377-w |
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