ArticleNature communications2020
A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
14 citing papers in PubMed.
- Charting the Future of Stereoselective Carbohydrate Synthesis: The Essential Role of Cross-Disciplinary Innovation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Enhanced Selectivity of Chalcogen Bonding over Halogen Bonding Catalyzed C-glycosylation Through Differentiated Intermediate Activation.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025Article
- Emerging Capabilities of Nonclassical Noncovalent Interactions and Asymmetric Catalysis in Stereoselective Glycosylations and Carbohydrate Functionalizations.Accounts of chemical research · 2025Article
- Article
- Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides.Journal of the American Chemical Society · 2024Article
- Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.Journal of the American Chemical Society · 2023Article
- A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol.Nature chemistry · 2023Article
- Halogen-bond-assisted radical activation of glycosyl donors enables mild and stereoconvergent 1,2-cis-glycosylation.Nature chemistry · 2022Article
- Pushing the Limits of Characterising a Weak Halogen Bond in Solution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Recent Advances in Stereoselective ChemicalFrontiers in molecular biosciences · 2022Review
- Exploiting non-covalent interactions in selective carbohydrate synthesis.Nature reviews. Chemistry · 2021Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of noncovalent halogen bonding (XB) catalysis is rapidly gaining traction, as isolated reports documented better performance than the well-established hydrogen bonding thiourea catalysis. However, convincing cases allowing XB activation to be competitive in challenging bond formations are lacking. Herein, we report a robust XB catalyzed 2-deoxyglycosylation, featuring a biomimetic reaction network indicative of dynamic XB activation. Benchmarking studies uncovered an improved substrate tolerance compared to thiourea-catalyzed protocols. Kinetic investigations reveal an autoinductive sigmoidal kinetic profile, supporting an in situ amplification of a XB dependent active catalytic species. Kinetic isotopic effect measurements further support quantum tunneling in the rate determining step. Furthermore, we demonstrate XB catalysis tunability via a halogen swapping strategy, facilitating 2-deoxyribosylations of D-ribals. This protocol showcases the clear emergence of XB catalysis as a versatile activation mode in noncovalent organocatalysis, and as an important addition to the catalytic toolbox of chemical glycosylations.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.