Evidence map›Paper›PMID 40447579›Full record

ArticleNature communications2025

Birch reductive arylation by mechanochemical anionic activation of polycyclic aromatic compounds.

Yoshifumi Toyama, Akiko Yagi, Kenichiro Itami, Hideto Ito

Abstract read
In one paragraph

Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Chemical science · 2026
    Article
  3. 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

4 authors.

Yoshifumi ToyamaDepartment of Chemistry, Graduate School of Science, Nagoya University, Nagoya, Japan.
Akiko YagiDepartment of Chemistry, Graduate School of Science, Nagoya University, Nagoya, Japan.ORCID http://orcid.org/0000-0003-2941-4357
Kenichiro ItamiInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Nagoya, Japan.ORCID http://orcid.org/0000-0001-5227-7894
Hideto ItoDepartment of Chemistry, Graduate School of Science, Nagoya University, Nagoya, Japan. ito.hideto.p4@f.mail.nagoya-u.ac.jp.ORCID http://orcid.org/0000-0002-4034-6247

Funding

MEXT | Japan Society for the Promotion of Science (JSPS) JP25H01408MEXT | Japan Society for the Promotion of Science (JSPS) JP25K01764MEXT | JST | Core Research for Evolutional Science and Technology (CREST) JPMJCR19R1Sumitomo Foundation 2300884
6 · The paper itself

Abstract

Birch reduction is a well-known process for transforming aromatic compounds. The reduction of aromatic rings using alkali metals produces anionic species that react with protons or electrophiles. Generally, this reaction is accompanied by significant limitations in the available nucleophiles, since in most cases only alkyl halides and silyl chlorides are available. In particular, the arylation of unfunctionalized polycyclic aromatic hydrocarbons (PAHs), so-called Birch reductive arylation, has not yet been investigated. Herein, we report a Birch reductive arylation by mechanochemical anionic activation using a lithium(0) wire, followed by addition of various fluoroarenes. Specifically, not only Birch reductive arylation products but also formal C-H arylation products can be obtained from unfunctionalized PAHs, achieving one-pot annulative π-extension to give nanographenes. This process is a unique reaction that is rarely achieved in solution, and shows the interesting reactivity of lithium metal and fluoroarenes in the solid state.

Identifiers

PMID40447579
PMCPMC12125365

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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.