Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis
Abstract Electro/photocatalytic C-N coupling acts as a key build-block to the next generation of chemicals like amides for wide applications in energy, pharmaceuticals and chemical industries. However, the uncontrolled intermediates coupling challenges the efficient amide production regarding yield...
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| Language: | English |
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Nature Portfolio
2025-04-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-58840-0 |
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| author | Xin Li Weiping Yang Junping Yue Jieyuan Li Shujie Shen Ruimin Chen Jielin Wang Huimin Dan Dagang Yu Fan Dong |
| author_facet | Xin Li Weiping Yang Junping Yue Jieyuan Li Shujie Shen Ruimin Chen Jielin Wang Huimin Dan Dagang Yu Fan Dong |
| author_sort | Xin Li |
| collection | DOAJ |
| description | Abstract Electro/photocatalytic C-N coupling acts as a key build-block to the next generation of chemicals like amides for wide applications in energy, pharmaceuticals and chemical industries. However, the uncontrolled intermediates coupling challenges the efficient amide production regarding yield or selectivity. Here we propose a photocatalytic radical addition route, where the fundamental active species, including oxygen and photogenerated electron-hole pairs, are regulated for selective intermediates generation and efficient acetamide synthesis from mild co-oxidation of CH3CH2OH and NH3. Sufficient CH3CH2OH is provided to accumulate the stable intermediate (CH3CHO). Meanwhile, the limited NH3 concentration ensures the controllable generation and fast addition of the transient radical (●NH2) on CH3CHO. Through the directed coupling of stable-transient intermediates, the acetamide synthesis rate is pushed forward to a hundred-mmol level (105.61 ± 4.86 mmol·gcat −1·h−1) with a selectivity of 99.17% ± 0.39%, reaching a gram-scale yield (1.82 g) of acetamide. These results illuminate valuable opportunities for the photocatalysis-driven synthetic industry. |
| format | Article |
| id | doaj-art-3a6be3fd93694225bf9f04d290c6010f |
| institution | OA Journals |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-3a6be3fd93694225bf9f04d290c6010f2025-08-20T02:28:10ZengNature PortfolioNature Communications2041-17232025-04-011611910.1038/s41467-025-58840-0Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesisXin Li0Weiping Yang1Junping Yue2Jieyuan Li3Shujie Shen4Ruimin Chen5Jielin Wang6Huimin Dan7Dagang Yu8Fan Dong9Research Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan UniversityResearch Center for Carbon-Neutral Environmental & Energy Technology, Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of ChinaAbstract Electro/photocatalytic C-N coupling acts as a key build-block to the next generation of chemicals like amides for wide applications in energy, pharmaceuticals and chemical industries. However, the uncontrolled intermediates coupling challenges the efficient amide production regarding yield or selectivity. Here we propose a photocatalytic radical addition route, where the fundamental active species, including oxygen and photogenerated electron-hole pairs, are regulated for selective intermediates generation and efficient acetamide synthesis from mild co-oxidation of CH3CH2OH and NH3. Sufficient CH3CH2OH is provided to accumulate the stable intermediate (CH3CHO). Meanwhile, the limited NH3 concentration ensures the controllable generation and fast addition of the transient radical (●NH2) on CH3CHO. Through the directed coupling of stable-transient intermediates, the acetamide synthesis rate is pushed forward to a hundred-mmol level (105.61 ± 4.86 mmol·gcat −1·h−1) with a selectivity of 99.17% ± 0.39%, reaching a gram-scale yield (1.82 g) of acetamide. These results illuminate valuable opportunities for the photocatalysis-driven synthetic industry.https://doi.org/10.1038/s41467-025-58840-0 |
| spellingShingle | Xin Li Weiping Yang Junping Yue Jieyuan Li Shujie Shen Ruimin Chen Jielin Wang Huimin Dan Dagang Yu Fan Dong Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis Nature Communications |
| title | Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis |
| title_full | Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis |
| title_fullStr | Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis |
| title_full_unstemmed | Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis |
| title_short | Photocatalytic C-N coupling from stable and transient intermediates for gram-scale acetamide synthesis |
| title_sort | photocatalytic c n coupling from stable and transient intermediates for gram scale acetamide synthesis |
| url | https://doi.org/10.1038/s41467-025-58840-0 |
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