Evidence map›Paper›PMID 28572912›Full record

ArticleChemical science2017

Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer.

John J Molloy, Thomas A Clohessy, Craig Irving, Niall A Anderson, Guy C Lloyd-Jones, Allan J B Watson

Abstract read
In one paragraph

Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.

0numbers the graph read from it
0cells of the map it votes in
12citing 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

12 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Indolylboronic Acids: Preparation and Applications.Molecules (Basel, Switzerland) · 2019
    Review
  8. Article
  9. Article
  10. Article
  11. Review
  12. 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.

John J MolloyDepartment of Pure and Applied Chemistry , WestCHEM , University of Strathclyde , 295 Cathedral Street , Glasgow , G1 1XL , UK . Email: allan.watson.100@strath.ac.uk.
Thomas A ClohessyDepartment of Pure and Applied Chemistry , WestCHEM , University of Strathclyde , 295 Cathedral Street , Glasgow , G1 1XL , UK . Email: allan.watson.100@strath.ac.uk.
Craig IrvingDepartment of Pure and Applied Chemistry , WestCHEM , University of Strathclyde , 295 Cathedral Street , Glasgow , G1 1XL , UK . Email: allan.watson.100@strath.ac.uk.
Niall A AndersonGlaxoSmithKline , Medicines Research Centre , Gunnels Wood Road , Stevenage , SG1 2NY , UK.
Guy C Lloyd-JonesSchool of Chemistry , University of Edinburgh West Mains Road , Edinburgh , EH9 3JJ , UK.
Allan J B WatsonDepartment of Pure and Applied Chemistry , WestCHEM , University of Strathclyde , 295 Cathedral Street , Glasgow , G1 1XL , UK . Email: allan.watson.100@strath.ac.uk.ORCID 0000-0002-1582-4286

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report the direct chemoselective Brown-type oxidation of aryl organoboron systems containing two oxidizable boron groups. Basic biphasic reaction conditions enable selective formation and phase transfer of a boronic acid trihydroxyboronate in the presence of boronic acid pinacol (BPin) esters, while avoiding speciation equilibria. Spectroscopic investigations validate a base-promoted phase-selective discrimination of organoboron species. This phenomenon is general across a broad range of organoboron compounds and can also be used to invert conventional protecting group strategies, enabling chemoselective oxidation of BMIDA species over normally more reactive BPin substrates. We also demonstrate the selective oxidation of diboronic acid systems with chemoselectivity predictable

Identifiers

PMID28572912
PMCPMC5452267

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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.