Evidence map›Paper›PMID 25558441›Full record

ArticleChemistryOpen2014

Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter.

Kohei Matsuzaki, Kenta Okuyama, Etsuko Tokunaga, Motoo Shiro, Norio Shibata

Erratum issuedAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ChemistryOpen, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Review
  2. Review
  3. Transition-Metal-FreeJACS Au · 2024
    Article
  4. Review
  5. Synthesis of fluoro-functionalized diaryl-λBeilstein journal of organic chemistry · 2018
    Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

5 authors.

Kohei MatsuzakiDepartment of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan) E-mail: nozshiba@nitech.ac.jp.
Kenta OkuyamaDepartment of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan) E-mail: nozshiba@nitech.ac.jp.
Etsuko TokunagaDepartment of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan) E-mail: nozshiba@nitech.ac.jp.
Motoo ShiroRigaku Corporation 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666 (Japan).
Norio ShibataDepartment of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan) E-mail: nozshiba@nitech.ac.jp.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A sterically demanding unsymmetrical pentafluorophenyl-triisopropylphenyl-λ(3)-iodane was developed as an effective reagent for the electrophilic pentafluorophenylation of various β-keto esters and a β-keto amide. 17 examples of α-pentafluorophenylated 1,3-dicarbonyl compounds 3 having a quaternary carbon center are provided. The resulting compounds were nicely transformed into chiral α-pentafluorophenyl ketones with an all-carbon stereogenic center in high yields and high enantioselectivities using asymmetric organocatalysis (up to 98 % ee) or asymmetric metal catalysis (up to 82 % ee).

Indexed as

asymmetric organocatalysisdiaryl-λ3-iodaneselectrophilic pentafluorophenylationpalladium

Identifiers

PMID25558441
PMCPMC4280821

What OpenQuestion holds

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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.