Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization
Abstract Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet to be fully explored. He...
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| Format: | Article |
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Nature Portfolio
2025-02-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56372-1 |
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| author | Si-Yuan Tang Zhan-Jie Wang Yu Ao Ning Wang Huan-Ming Huang |
| author_facet | Si-Yuan Tang Zhan-Jie Wang Yu Ao Ning Wang Huan-Ming Huang |
| author_sort | Si-Yuan Tang |
| collection | DOAJ |
| description | Abstract Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet to be fully explored. Herein, we present a successful description of a photoredox/Cr-catalyzed enantioselective three-component (hetero)arylalkylation of 1,3-dienes through C-H functionalization. A diverse array of chiral homoallylic alcohols could be obtained in good to excellent yields, accompanied by outstanding enantioselectivity. The asymmetric radical-polar crossover transformation could build two chiral centers simultaneously and demonstrates broad substrate tolerance, accommodating various drug-derived aldehydes, (hetero)aromatics, and 1,3-diene derivatives. Preliminary mechanistic studies indicate the involvement of a radical intermediate, with the chiral allylic chromium species reacting with various aliphatic and aromatic aldehydes through Zimmerman–Traxler transition states enabled by dual photoredox and chiral chromium catalysis. |
| format | Article |
| id | doaj-art-bf9b6c209a38461bb4aa19bf84add0d0 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-bf9b6c209a38461bb4aa19bf84add0d02025-02-09T12:45:06ZengNature PortfolioNature Communications2041-17232025-02-011611910.1038/s41467-025-56372-1Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalizationSi-Yuan Tang0Zhan-Jie Wang1Yu Ao2Ning Wang3Huan-Ming Huang4School of Physical Science and Technology, ShanghaiTech UniversitySchool of Physical Science and Technology, ShanghaiTech UniversitySchool of Physical Science and Technology, ShanghaiTech UniversitySchool of Physical Science and Technology, ShanghaiTech UniversitySchool of Physical Science and Technology, ShanghaiTech UniversityAbstract Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet to be fully explored. Herein, we present a successful description of a photoredox/Cr-catalyzed enantioselective three-component (hetero)arylalkylation of 1,3-dienes through C-H functionalization. A diverse array of chiral homoallylic alcohols could be obtained in good to excellent yields, accompanied by outstanding enantioselectivity. The asymmetric radical-polar crossover transformation could build two chiral centers simultaneously and demonstrates broad substrate tolerance, accommodating various drug-derived aldehydes, (hetero)aromatics, and 1,3-diene derivatives. Preliminary mechanistic studies indicate the involvement of a radical intermediate, with the chiral allylic chromium species reacting with various aliphatic and aromatic aldehydes through Zimmerman–Traxler transition states enabled by dual photoredox and chiral chromium catalysis.https://doi.org/10.1038/s41467-025-56372-1 |
| spellingShingle | Si-Yuan Tang Zhan-Jie Wang Yu Ao Ning Wang Huan-Ming Huang Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization Nature Communications |
| title | Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization |
| title_full | Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization |
| title_fullStr | Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization |
| title_full_unstemmed | Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization |
| title_short | Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization |
| title_sort | photoredox cr catalyzed enantioselective radical polar crossover transformation via c h functionalization |
| url | https://doi.org/10.1038/s41467-025-56372-1 |
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