Evidence map›Paper›PMID 38882554›Full record

ArticleChem2023

Phosphorus fluoride exchange: Multidimensional catalytic click chemistry from phosphorus connective hubs.

Shoujun Sun, Joshua A Homer, Christopher J Smedley, Qing-Qing Cheng, K Barry Sharpless, John E Moses

Abstract read
In one paragraph

Article in Chem, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.

0numbers the graph read from it
0cells of the map it votes in
21citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

21 citing papers in PubMed.

  1. Review
  2. Review
  3. Article
  4. Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Article
  10. Diversity Oriented Clicking for Modular Synthesis.Nature reviews. Methods primers · 2025
    Article
  11. Article
  12. Article
  13. Chloroimidazolium Deoxyfluorination Reagent with HThe Journal of organic chemistry · 2024
    Article
  14. Review
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Shoujun SunCancer Center, Cold Spring Harbor Laboratory, 1 Bungtown Road, Cold Spring Harbor, NY 11724, USA.
Joshua A HomerCancer Center, Cold Spring Harbor Laboratory, 1 Bungtown Road, Cold Spring Harbor, NY 11724, USA.
Christopher J SmedleyLa Trobe Institute for Molecular Science, La Trobe University, Bundoora, Melbourne, VIC 3086, Australia.
Qing-Qing ChengDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
K Barry SharplessDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
John E MosesCancer Center, Cold Spring Harbor Laboratory, 1 Bungtown Road, Cold Spring Harbor, NY 11724, USA.

Funding

Single-Cell Biology Shared ResourceP30CA045508 · NCI · COLD SPRING HARBOR LABORATORY · PI John Edward Moses · 1987 to 2026
$118.9M
Sulfur(VI) Fluoride Exchange (SuFEx): new developments and biological applicationsR01GM117145 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI SHARPLESS, KARL BARRY · 2016 to 2023
$3.9M
NCI NIH HHS P30 CA045508NIGMS NIH HHS R01 GM117145
6 · The paper itself

Abstract

Phosphorus Fluoride Exchange (PFEx) represents a cutting-edge advancement in catalytic click-reaction technology. Drawing inspiration from Nature's phosphate connectors, PFEx facilitates the reliable coupling of P(V)-F loaded hubs with aryl alcohols, alkyl alcohols, and amines to produce stable, multidimensional P(V)-O and P(V)-N linked products. The rate of P-F exchange is significantly enhanced by Lewis amine base catalysis, such as 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). PFEx substrates containing multiple P-F bonds are capable of selective, serial exchange reactions via judicious catalyst selection. In fewer than four synthetic steps, controlled projections can be deliberately incorporated along three of the four tetrahedral axes departing from the P(V) central hub, thus taking full advantage of the potential for generating three-dimensional diversity. Furthermore, late-stage functionalization of drugs and drug fragments can be achieved with the polyvalent PFEx hub, hexafluorocyclotriphosphazene (HFP), as has been demonstrated in prior research.

Identifiers

PMID38882554
PMCPMC11172371

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Registered trials

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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.