ArticleOrganic & biomolecular chemistry2021
Palladium(II)-assisted activation of thioglycosides.
Article in Organic & biomolecular chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 12 citations in OpenAlex.
- Article
- Cooperatively Catalyzed Activation of Thioglycosides with Iodine and Iron(III) Trifluoromethanesulfonate.Molecules (Basel, Switzerland) · 2025Article
- Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides.Molecules (Basel, Switzerland) · 2024Article
- Direct Synthesis of Glycosyl Chlorides from Thioglycosides.The Journal of organic chemistry · 2024Article
- Expedient Synthesis of Superarmed Glycosyl Donors via Oxidative Thioglycosidation of Glycals.Synthesis · 2024Article
- Activation of Thioglycosides with Copper(II) Bromide.Molecules (Basel, Switzerland) · 2022Article
- HPLC-Based Automated Synthesis of Glycans in Solution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Described herein is the first example of glycosidation of thioglycosides in the presence of palladium(ii) bromide. While the activation with PdBr2 alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylations were performed in the presence of propargyl bromide as an additive. Preliminary mechanistic studies suggest that propargyl bromide assists the reaction by creating an ionizing complex, which accelerates the leaving group departure. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this new reaction. Selective and chemoselective activation of thioglycosides over other leaving groups has also been explored.
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Registered trials
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