Electrochemical Bromination of Glycals
Herein, the convenient one-step electrochemical bromination of glycals using Bu4NBr as the brominating source under metal-catalyst-free and oxidant-free reaction conditions was described. A series of 2-bromoglycals bearing different electron-withdrawing or electron-donating protective groups were su...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2021-12-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.796690/full |
| _version_ | 1819096668057894912 |
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| author | Zhao-Xiang Luo Miao Liu Tian Li De-Cai Xiong De-Cai Xiong Xin-Shan Ye |
| author_facet | Zhao-Xiang Luo Miao Liu Tian Li De-Cai Xiong De-Cai Xiong Xin-Shan Ye |
| author_sort | Zhao-Xiang Luo |
| collection | DOAJ |
| description | Herein, the convenient one-step electrochemical bromination of glycals using Bu4NBr as the brominating source under metal-catalyst-free and oxidant-free reaction conditions was described. A series of 2-bromoglycals bearing different electron-withdrawing or electron-donating protective groups were successfully synthesized in moderate to excellent yields. The coupling of tri-O-benzyl-2-bromogalactal with phenylacetylene, potassium phenyltrifluoroborate, or a 6-OH acceptor was achieved to afford 2C-branched carbohydrates and disaccharides via Sonogashira coupling, Suzuki coupling, and Ferrier rearrangement reactions with high efficiency. The radical trapping and cyclic voltammetry experiments indicated that bromine radicals may be involved in the reaction process. |
| first_indexed | 2024-12-22T00:02:51Z |
| format | Article |
| id | doaj.art-d53c72a60672437fbe37f90ff9f169b2 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T00:02:51Z |
| publishDate | 2021-12-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-d53c72a60672437fbe37f90ff9f169b22022-12-21T18:45:38ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-12-01910.3389/fchem.2021.796690796690Electrochemical Bromination of GlycalsZhao-Xiang Luo0Miao Liu1Tian Li2De-Cai Xiong3De-Cai Xiong4Xin-Shan Ye5State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, ChinaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, ChinaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, ChinaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, ChinaState Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing, ChinaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, ChinaHerein, the convenient one-step electrochemical bromination of glycals using Bu4NBr as the brominating source under metal-catalyst-free and oxidant-free reaction conditions was described. A series of 2-bromoglycals bearing different electron-withdrawing or electron-donating protective groups were successfully synthesized in moderate to excellent yields. The coupling of tri-O-benzyl-2-bromogalactal with phenylacetylene, potassium phenyltrifluoroborate, or a 6-OH acceptor was achieved to afford 2C-branched carbohydrates and disaccharides via Sonogashira coupling, Suzuki coupling, and Ferrier rearrangement reactions with high efficiency. The radical trapping and cyclic voltammetry experiments indicated that bromine radicals may be involved in the reaction process.https://www.frontiersin.org/articles/10.3389/fchem.2021.796690/fullelectrochemistrybrominationglycals2-bromoglycalscross-couplingferrier rearrangement |
| spellingShingle | Zhao-Xiang Luo Miao Liu Tian Li De-Cai Xiong De-Cai Xiong Xin-Shan Ye Electrochemical Bromination of Glycals Frontiers in Chemistry electrochemistry bromination glycals 2-bromoglycals cross-coupling ferrier rearrangement |
| title | Electrochemical Bromination of Glycals |
| title_full | Electrochemical Bromination of Glycals |
| title_fullStr | Electrochemical Bromination of Glycals |
| title_full_unstemmed | Electrochemical Bromination of Glycals |
| title_short | Electrochemical Bromination of Glycals |
| title_sort | electrochemical bromination of glycals |
| topic | electrochemistry bromination glycals 2-bromoglycals cross-coupling ferrier rearrangement |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.796690/full |
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