Evidence map›Paper›PMID 37653231›Full record

ArticleNature chemistry2023

Ortho-C-H methoxylation of aryl halides enabled by a polarity-reversed N-O reagent.

Xin Liu, Yue Fu, Zhijie Chen, Peng Liu, Guangbin Dong

Abstract read
In one paragraph

Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. 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. Article
  2. Article
  3. Article
  4. Meta-Dimethylation of Arenes via Catellani Reaction from Aryl Thianthrenium Salts.Angewandte Chemie (International ed. in English) · 2025
    Article
  5. 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

5 authors.

Xin LiuDepartment of Chemistry, University of Chicago, Chicago, IL, USA.ORCID http://orcid.org/0000-0001-8355-4217
Yue FuDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA, USA.ORCID http://orcid.org/0000-0003-3085-7817
Zhijie ChenDepartment of Chemistry, University of Chicago, Chicago, IL, USA.
Peng LiuDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA, USA. pengliu@pitt.edu.ORCID http://orcid.org/0000-0002-8188-632X
Guangbin DongDepartment of Chemistry, University of Chicago, Chicago, IL, USA. gbdong@uchicago.edu.ORCID http://orcid.org/0000-0003-1331-6015

Funding

New Directions in Palladium/Norbornene Cooperative-RenewalR01GM124414 · NIGMS · UNIVERSITY OF CHICAGO · PI DONG, GUANGBIN · 2018 to 2025
$2.6M
NIGMS NIH HHS R01 GM124414
6 · The paper itself

Abstract

Oxygen-substituted arenes widely exist in biologically important molecules and can serve as versatile handles to install other functional groups. However, direct and site-selective installation of oxygen groups to common aromatic compounds remains challenging, especially when additional arene functionalization is simultaneously required. Current arene C-H oxidation strategies generally require directing groups or precisely prefunctionalized substrates to control site-selectivity. While palladium/norbornene cooperative catalysis is promising for site-specific arene vicinal difunctionalization through simultaneous reactions with an electrophile and a nucleophile, the electrophile scope has been limited to species based on relatively 'soft' elements, such as carbon, nitrogen and sulfur. Here we report the development of an ortho oxygenation reaction with common aryl halides to rapidly deliver diverse aryl ethers. The coupling of the 'hard' oxygen electrophile is enabled by a stable, polarity-reversed, conformationally predistorted N-O reagent and facilitated by a C7-bromo-substituted norbornene mediator. Mechanistic studies reveal a unique S

Identifiers

PMID37653231
PMCPMC10973943

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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.