Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent
Abstract The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-hete...
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| Format: | Article |
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Nature Portfolio
2024-10-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-53202-8 |
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| author | Mingrui Li Yingtao Wu Xiao Song Jiaqiong Sun Zuxiao Zhang Guangfan Zheng Qian Zhang |
| author_facet | Mingrui Li Yingtao Wu Xiao Song Jiaqiong Sun Zuxiao Zhang Guangfan Zheng Qian Zhang |
| author_sort | Mingrui Li |
| collection | DOAJ |
| description | Abstract The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C–N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C–C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes. |
| format | Article |
| id | doaj-art-49895cf579074f7face158357bf7e2ac |
| institution | OA Journals |
| issn | 2041-1723 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-49895cf579074f7face158357bf7e2ac2025-08-20T02:17:47ZengNature PortfolioNature Communications2041-17232024-10-011511910.1038/s41467-024-53202-8Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagentMingrui Li0Yingtao Wu1Xiao Song2Jiaqiong Sun3Zuxiao Zhang4Guangfan Zheng5Qian Zhang6Department of Chemistry, Northeast Normal UniversityDepartment of Chemistry, Northeast Normal UniversityDepartment of Chemistry, Northeast Normal UniversityDepartment of Chemistry, Northeast Normal UniversityDepartment of Chemistry, University of Hawai’i at Mānoa. 2545 McCarthy MallDepartment of Chemistry, Northeast Normal UniversityDepartment of Chemistry, Northeast Normal UniversityAbstract The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C–N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C–C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes.https://doi.org/10.1038/s41467-024-53202-8 |
| spellingShingle | Mingrui Li Yingtao Wu Xiao Song Jiaqiong Sun Zuxiao Zhang Guangfan Zheng Qian Zhang Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent Nature Communications |
| title | Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent |
| title_full | Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent |
| title_fullStr | Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent |
| title_full_unstemmed | Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent |
| title_short | Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent |
| title_sort | visible light mediated organocatalyzed 1 3 aminoacylation of cyclopropane employing n benzoyl saccharin as bifunctional reagent |
| url | https://doi.org/10.1038/s41467-024-53202-8 |
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