ArticleAngewandte Chemie (International ed. in English)2021
Bioorthogonal Hydroamination of Push-Pull-Activated Linear Alkynes.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Synthesis of Novel Acetylene-Containing Phosphonates, Their Antiviral Activity, and Their Cytotoxicity to Different Cancer Cell Lines.Molecules (Basel, Switzerland) · 2026Article
- Development and Optimization of an Aminooxy Coupling Reaction to Prepare Multivalent Bioconjugates with a Single Noncanonical Amino Acid.Bioconjugate chemistry · 2026Article
- Strategy-Level Prodrug Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Development of Bioorthogonally Degradable Tough Hydrogels Using Enamine N-Oxide Based Crosslinkers.Advanced materials (Deerfield Beach, Fla.) · 2025Article
- Article
- EnamineSynlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Synthesis of push-pull-activated ynol ethers and their evaluation in the bioorthogonal hydroamination reaction.Organic & biomolecular chemistry · 2022Article
- Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
A bioorthogonal reaction between N,N-dialkylhydroxylamines and push-pull-activated halogenated alkynes is described. We explore the use of rehybridization effects in activating alkynes, and we show that electronic effects, when competing stereoelectronic and inductive factors are properly balanced, sufficiently activate a linear alkyne in the uncatalyzed conjugative retro-Cope elimination reaction while adequately protecting it against cellular nucleophiles. This design preserves the low steric profile of an alkyne and pairs it with a comparably unobtrusive hydroxylamine. The kinetics are on par with those of the fastest strain-promoted azide-alkyne cycloaddition reactions, the products regioselectively formed, the components sufficiently stable and easily installed, and the reaction suitable for cellular labeling.
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Registered trials
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