Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides.

Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides.
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DOI:
10.1039/d1ob00093d
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发表时间:
2021-04-14
影响因子:
3.2
通讯作者:
Demchenko AV
Demchenko AV
中科院分区:
化学3区
文献类型:
--
作者:
Steber HB;Singh Y;Demchenko AV

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本文提出的发现是三氟甲磺酸铋(III)(Bi(OTf)3)是用于活化糖基溴和糖基氯的有效催化剂。开发该方法的关键目标是以最低可能的量仅使用一种促进剂,并避免使用除分子筛之外的任何添加剂/助催化剂/酸清除剂。Bi(OTf)3在促进差异保护的葡糖基、半乳糖基和甘露糖基卤化物与许多类别的糖基受体的糖苷化方面效果良好。在仅35%的绿色和光稳定的Bi(OTf)3催化剂存在下,大多数反应在1小时内完成。
Presented herein is the discovery that bismuth(III) trifluoromethanesulfonate (Bi(OTf)3) is an effective catalyst for the activation of glycosyl bromides and glycosyl chlorides. The key objective for the development of this methodology is to employ only one promoter in the lowest possible amount and to avoid using any additive/co-catalyst/acid scavenger except molecular sieves. Bi(OTf)3 works well in promoting the glycosidation of differentially protected glucosyl, galactosyl, and mannosyl halides with many classes of glycosyl acceptors. Most reactions complete within 1 h in the presence of only 35% of green and light-stable Bi(OTf)3 catalyst.
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期刊: ORGANIC LETTERS
影响因子: 5.2
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