Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols
Abstract Cyclopropane fragments, which widely exist in marketed drugs and natural products, can confer special pharmacological properties to small‐molecule drugs. Therefore, developing methods to construct cyclopropanes is of great significance. Nevertheless, the introduction of cyclopropane primari...
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| Format: | Article |
| Language: | English |
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Wiley
2025-01-01
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| Series: | Advanced Science |
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| Online Access: | https://doi.org/10.1002/advs.202411788 |
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| author | Yongsheng Zhang Jincheng Wang Xiaoyan He Shilin Peng Lei Yuan Gang Huang Yongjin Guo Xiuhong Lu |
| author_facet | Yongsheng Zhang Jincheng Wang Xiaoyan He Shilin Peng Lei Yuan Gang Huang Yongjin Guo Xiuhong Lu |
| author_sort | Yongsheng Zhang |
| collection | DOAJ |
| description | Abstract Cyclopropane fragments, which widely exist in marketed drugs and natural products, can confer special pharmacological properties to small‐molecule drugs. Therefore, developing methods to construct cyclopropanes is of great significance. Nevertheless, the introduction of cyclopropane primarily relies on already‐formed cyclopropyl groups, which significantly restricts the diversity of cyclopropane skeletons. Late‐stage direct cyclopropanation is still a challenging task. Herein, a photo‐induced intermolecular deoxycyclopropanation reaction that employs alcohols as substrates, and 1 mol.% of 2,3,5,6‐tetrakis(carbazol‐9‐yl)‐1,4‐dicyanobenzene (4CzTPN) as organophotocatalyst is reported. This method proceeds with high transformation efficiency (up to 98% yield) and exhibits broad functional group tolerance, such as primary, secondary, and tertiary alcohols as well as various activated β‐halogenated alkenes. This process is mild, easy to operate, and has low equipment requirements. The power of this technology is demonstrated by the late‐stage functionalization of five marketed drugs and five natural products. |
| format | Article |
| id | doaj-art-29946ed64d4f4285b136cdb853fb0c20 |
| institution | Kabale University |
| issn | 2198-3844 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Advanced Science |
| spelling | doaj-art-29946ed64d4f4285b136cdb853fb0c202025-01-09T11:44:46ZengWileyAdvanced Science2198-38442025-01-01121n/an/a10.1002/advs.202411788Organophotocatalyst Enabled Deoxycyclopropanation of AlcoholsYongsheng Zhang0Jincheng Wang1Xiaoyan He2Shilin Peng3Lei Yuan4Gang Huang5Yongjin Guo6Xiuhong Lu7Shanghai Key Laboratory of Molecular Imaging Jiading District Central Hospital Affiliated Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaKey Laboratory of Structure‐Based Drug Design & Discovery of Ministry of Education Shenyang Pharmaceutical University Shenyang 110016 P. R. ChinaShanghai Key Laboratory of Molecular Imaging Jiading District Central Hospital Affiliated Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaShanghai Key Laboratory of Molecular Imaging Jiading District Central Hospital Affiliated Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaKey Laboratory of Structure‐Based Drug Design & Discovery of Ministry of Education Shenyang Pharmaceutical University Shenyang 110016 P. R. ChinaShanghai Key Laboratory of Molecular Imaging Jiading District Central Hospital Affiliated Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaSchool of Pharmacy Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaShanghai Key Laboratory of Molecular Imaging Jiading District Central Hospital Affiliated Shanghai University of Medicine and Health Sciences Shanghai 201318 P. R. ChinaAbstract Cyclopropane fragments, which widely exist in marketed drugs and natural products, can confer special pharmacological properties to small‐molecule drugs. Therefore, developing methods to construct cyclopropanes is of great significance. Nevertheless, the introduction of cyclopropane primarily relies on already‐formed cyclopropyl groups, which significantly restricts the diversity of cyclopropane skeletons. Late‐stage direct cyclopropanation is still a challenging task. Herein, a photo‐induced intermolecular deoxycyclopropanation reaction that employs alcohols as substrates, and 1 mol.% of 2,3,5,6‐tetrakis(carbazol‐9‐yl)‐1,4‐dicyanobenzene (4CzTPN) as organophotocatalyst is reported. This method proceeds with high transformation efficiency (up to 98% yield) and exhibits broad functional group tolerance, such as primary, secondary, and tertiary alcohols as well as various activated β‐halogenated alkenes. This process is mild, easy to operate, and has low equipment requirements. The power of this technology is demonstrated by the late‐stage functionalization of five marketed drugs and five natural products.https://doi.org/10.1002/advs.2024117884CzTPNcyclopropanedeoxycyclopropanationNHC alcohol adductsphotocatalysis |
| spellingShingle | Yongsheng Zhang Jincheng Wang Xiaoyan He Shilin Peng Lei Yuan Gang Huang Yongjin Guo Xiuhong Lu Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols Advanced Science 4CzTPN cyclopropane deoxycyclopropanation NHC alcohol adducts photocatalysis |
| title | Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols |
| title_full | Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols |
| title_fullStr | Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols |
| title_full_unstemmed | Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols |
| title_short | Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols |
| title_sort | organophotocatalyst enabled deoxycyclopropanation of alcohols |
| topic | 4CzTPN cyclopropane deoxycyclopropanation NHC alcohol adducts photocatalysis |
| url | https://doi.org/10.1002/advs.202411788 |
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