Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2
Abstract An unprecedented Et2Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond of cyclopropanols with CO2 is disclosed, which provides a straightforward and efficient methodology for the synthesis of a variety of structurally diverse and useful malonic acids in moderate to excellent yields. The...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2024-03-01
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| Series: | Advanced Science |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/advs.202307633 |
| _version_ | 1797271792872587264 |
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| author | Hongjian Liu Lei Shi Xiaobin Tan Bangxiong Kang Gen Luo Huanfeng Jiang Chaorong Qi |
| author_facet | Hongjian Liu Lei Shi Xiaobin Tan Bangxiong Kang Gen Luo Huanfeng Jiang Chaorong Qi |
| author_sort | Hongjian Liu |
| collection | DOAJ |
| description | Abstract An unprecedented Et2Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond of cyclopropanols with CO2 is disclosed, which provides a straightforward and efficient methodology for the synthesis of a variety of structurally diverse and useful malonic acids in moderate to excellent yields. The protocol features mild reaction conditions, excellent functional group compatibility, broad substrate scope, and facile derivatization of the products. DFT calculations confirm that the transition‐metal‐free transformation proceeds through a novel ring‐opening/α‐functionalization/ring‐closing/ring‐opening/β‐functionalization (ROFCOF) process, and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) plays dual important roles in the transformation. |
| first_indexed | 2024-03-07T14:13:21Z |
| format | Article |
| id | doaj.art-248c4f9a0552401ebd3e32a12904c2f3 |
| institution | Directory Open Access Journal |
| issn | 2198-3844 |
| language | English |
| last_indexed | 2024-03-07T14:13:21Z |
| publishDate | 2024-03-01 |
| publisher | Wiley |
| record_format | Article |
| series | Advanced Science |
| spelling | doaj.art-248c4f9a0552401ebd3e32a12904c2f32024-03-06T14:04:50ZengWileyAdvanced Science2198-38442024-03-01119n/an/a10.1002/advs.202307633Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2Hongjian Liu0Lei Shi1Xiaobin Tan2Bangxiong Kang3Gen Luo4Huanfeng Jiang5Chaorong Qi6Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 ChinaInstitutes of Physical Science and Information Technology Anhui University Hefei 230601 ChinaKey Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 ChinaKey Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 ChinaInstitutes of Physical Science and Information Technology Anhui University Hefei 230601 ChinaKey Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 ChinaKey Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 ChinaAbstract An unprecedented Et2Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond of cyclopropanols with CO2 is disclosed, which provides a straightforward and efficient methodology for the synthesis of a variety of structurally diverse and useful malonic acids in moderate to excellent yields. The protocol features mild reaction conditions, excellent functional group compatibility, broad substrate scope, and facile derivatization of the products. DFT calculations confirm that the transition‐metal‐free transformation proceeds through a novel ring‐opening/α‐functionalization/ring‐closing/ring‐opening/β‐functionalization (ROFCOF) process, and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) plays dual important roles in the transformation.https://doi.org/10.1002/advs.202307633carbon dioxidecyclopropanolsdicarboxylationmalonic acids |
| spellingShingle | Hongjian Liu Lei Shi Xiaobin Tan Bangxiong Kang Gen Luo Huanfeng Jiang Chaorong Qi Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 Advanced Science carbon dioxide cyclopropanols dicarboxylation malonic acids |
| title | Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 |
| title_full | Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 |
| title_fullStr | Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 |
| title_full_unstemmed | Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 |
| title_short | Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 |
| title_sort | et2zn mediated gem dicarboxylation of cyclopropanols with co2 |
| topic | carbon dioxide cyclopropanols dicarboxylation malonic acids |
| url | https://doi.org/10.1002/advs.202307633 |
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