ArticleACS central science2020
Catalytic Chemoselective
Article in ACS central science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Post-translational modifications of silk proteins.RSC chemical biology · 2026Review
- Phosphate-bridged CNT/TiOiScience · 2026Article
- Synthesis of diaryl phosphates using phytic acid as a phosphorus source.Beilstein journal of organic chemistry · 2026Article
- Synthesis of Acinetobacter baumannii Lipid A(s) and derivatives and their structure-immunostimulatory activity relationships.Communications chemistry · 2025Article
- Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis.Organic letters · 2025Article
- A New Process for the Synthesis of Budesonide 21-Phosphate and Evaluation in a Murine Model of Inflammation.Molecules (Basel, Switzerland) · 2024Article
- A highly efficient catalytic method for the synthesis of phosphite diesters.Chemical science · 2024Article
- Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base.RSC advances · 2023Article
- Article
- Total Synthesis and Prediction of Ulodione Natural Products Guided by DFT Calculations.Angewandte Chemie (International ed. in English) · 2022Article
- Mild and Chemoselective Phosphorylation of Alcohols Using a Ψ-Reagent.Organic letters · 2021Article
- Nature Chose Phosphates and Chemists Should Too: How Emerging P(V) Methods Can Augment Existing Strategies.ACS central science · 2021Review
- A Phosphoramidate Strategy Enables Membrane Permeability of a Non-nucleotide Inhibitor of the Prolyl Isomerase Pin1.ACS medicinal chemistry letters · 2020Article
- Let's Make White Phosphorus Obsolete.ACS central science · 2020Review
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Phosphorylation of alcohols is a fundamentally important reaction in both life science and physical science. Product phosphate monoesters play key roles in living organisms, natural products, pharmaceuticals, and organic materials. Most of the chemical methods to date for synthesizing phosphate monoesters, however, require multistep sequences or are limited to specific types of substrates possibly due to harsh conditions. An alternative way to enable the simple production of phosphate monoesters from highly functionalized precursor alcohols is, thus, highly desired. We report herein a catalytic phosphorylation of alcohols with high functional group tolerance using tetrabutylammonium hydrogen sulfate (TBAHS) and phosphoenolpyruvic acid monopotassium salt (PEP-K) as the catalyst and phosphoryl donor, respectively. This method enables the direct introduction of a nonprotected phosphate group to the hydroxy group of a diverse menu of alcohol substrates, including functionalized small molecules, carbohydrates, and unprotected peptides. Nuclear magnetic resonance, mass spectrometric, and density functional theory analyses suggest that an unprecedented mixed anhydride species, generated from PEP-K and TBAHS, acts as an active phosphoryl donor in this reaction. This operationally simple and chemoselective catalytic phosphorylation allows for the efficient production of densely functionalized
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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.