Hydrodehalogenation of aryl halides through direct electrolysis
A catalyst- and metal-free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu3 N/Et3 N behave as effective reductants and hydrogen atom...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/137824 |
| _version_ | 1826116202723803136 |
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| author | Ke, Jie Wang, Hongling Zhou, Liejin Mou, Chengli Zhang, Jingjie Pan, Lutai Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Ke, Jie Wang, Hongling Zhou, Liejin Mou, Chengli Zhang, Jingjie Pan, Lutai Chi, Robin Yonggui |
| author_sort | Ke, Jie |
| collection | NTU |
| description | A catalyst- and metal-free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu3 N/Et3 N behave as effective reductants and hydrogen atom donors for this electrochemical reductive reaction. Various aryl and heteroaryl bromides worked effectively. The typically less reactive aryl chlorides and fluorides can also be smoothly converted. The utility of our method is demonstrated by detoxification of harmful pesticides and hydrodebromination of a dibrominated biphenyl (analogues of flame-retardants) in gram scale. |
| first_indexed | 2024-10-01T04:07:29Z |
| format | Journal Article |
| id | ntu-10356/137824 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:07:29Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1378242023-02-28T19:47:20Z Hydrodehalogenation of aryl halides through direct electrolysis Ke, Jie Wang, Hongling Zhou, Liejin Mou, Chengli Zhang, Jingjie Pan, Lutai Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry::Organic electrochemistry Electrochemistry Hydrodehalogenation A catalyst- and metal-free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu3 N/Et3 N behave as effective reductants and hydrogen atom donors for this electrochemical reductive reaction. Various aryl and heteroaryl bromides worked effectively. The typically less reactive aryl chlorides and fluorides can also be smoothly converted. The utility of our method is demonstrated by detoxification of harmful pesticides and hydrodebromination of a dibrominated biphenyl (analogues of flame-retardants) in gram scale. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-15T09:18:58Z 2020-04-15T09:18:58Z 2019 Journal Article Ke, J., Wang, H., Zhou, L., Mou, C., Zhang, J., Pan, L., & Chi, R. Y. (2019). Hydrodehalogenation of aryl halides through direct electrolysis. Chemistry – A European Journal, 25(28), 6911-6914. doi:10.1002/chem.201901082 0947-6539 https://hdl.handle.net/10356/137824 10.1002/chem.201901082 30950097 2-s2.0-85065185155 28 25 6911 6914 en Chemistry – A European Journal This is the peer reviewed version of the following article: Ke, J., Wang, H., Zhou, L., Mou, C., Zhang, J., Pan, L., & Chi, R. Y. (2019). Hydrodehalogenation of aryl halides through direct electrolysis. Chemistry – A European Journal, 25(28), 6911-6914, which has been published in final form at https://doi.org/10.1002/chem.201901082. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry::Organic electrochemistry Electrochemistry Hydrodehalogenation Ke, Jie Wang, Hongling Zhou, Liejin Mou, Chengli Zhang, Jingjie Pan, Lutai Chi, Robin Yonggui Hydrodehalogenation of aryl halides through direct electrolysis |
| title | Hydrodehalogenation of aryl halides through direct electrolysis |
| title_full | Hydrodehalogenation of aryl halides through direct electrolysis |
| title_fullStr | Hydrodehalogenation of aryl halides through direct electrolysis |
| title_full_unstemmed | Hydrodehalogenation of aryl halides through direct electrolysis |
| title_short | Hydrodehalogenation of aryl halides through direct electrolysis |
| title_sort | hydrodehalogenation of aryl halides through direct electrolysis |
| topic | Science::Chemistry::Organic chemistry::Organic electrochemistry Electrochemistry Hydrodehalogenation |
| url | https://hdl.handle.net/10356/137824 |
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