Stereoselective Aromatic O-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere.
Stereoselective Aromatic O-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere.
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DOI：
10.1021/acs.joc.3c00776
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发表时间：
2023-07
期刊：
影响因子：
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通讯作者：
Jinsheng Lai;Shuqin Wu;Zhuoyi Zhou;Hui Liu;Yuanhong Tu;Qingju Zhang;Liming Wang
中科院分区：
文献类型：
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作者：
Jinsheng Lai;Shuqin Wu;Zhuoyi Zhou;Hui Liu;Yuanhong Tu;Qingju Zhang;Liming Wang
在空气气氛下，以氯代糖基和芳基硼酸为原料，钯为催化剂，制备了一种新颖的β-选择性邻芳基糖基化反应。该反应对水分不敏感，并以易于获得且稳定的氯糖基和芳基硼酸为底物进行表征。多种底物范围，包括各种芳基硼酸和糖基氯供体，在该方法中具有良好的耐受性。芳香硼酸在空气中被O2氧化生成苯酚作为芳香源。该方法为高效合成具有生物活性的o -芳基糖苷提供了一条新的途径，在今后的研究中具有广泛的应用前景。
A novel exclusive β-selective O-aryl glycosylation was developed using glycosyl chloride and arylboronic acid with a palladium catalyst under an air atmosphere. The reaction was insensitive to moisture and characterized using readily available and bench-stable glycosyl chloride and arylboronic acid as substrates. A diverse range of substrate scopes, including various arylboronic acids and glycosyl chloride donors, was well-tolerated in this method. Arylboronic acid was oxidized by O2 in air to produce phenol as the aromatic source. This new strategy provides an alternative route and may find broad applications in efficient synthesis of bioactive O-aryl glycosides in the future.