Electrochemical Bromination of Glycals.
Electrochemical Bromination of Glycals.
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乙二醇的电化学溴化
DOI：
10.3389/fchem.2021.796690
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发表时间：
2021
影响因子：
5.5
通讯作者：
Ye XS
中科院分区：
文献类型：
--
作者：
Luo ZX;Liu M;Li T;Xiong DC;Ye XS
本文描述了在无金属催化剂和无氧化剂的反应条件下，以Bu 4 NBr为溴化源，方便地对糖基进行一步电化学溴化。以中等至优异的产率成功地合成了一系列带有不同吸电子或供电子保护基的2-溴代甘醛。三-O-苄基-2-溴代半乳糖醛与苯乙炔、苯三氟硼酸钾或6-OH受体通过Sonogashira偶联、Suzuki偶联和Ferrier重排反应高效地偶联得到2C-支链碳水化合物和二糖。自由基捕获和循环伏安实验表明，溴自由基可能参与了反应过程。
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.