Evidence map›Paper›PMID 35138096›Full record

ArticleJournal of the American Chemical Society2022

Catalytic Activation of Unstrained C(Aryl)-C(Alkyl) Bonds in 2,2'-Methylenediphenols.

Jun Zhu, Yibin Xue, Rui Zhang, Benjamin L Ratchford, Guangbin Dong

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2022. 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. Hydrogen transfer-triggered C(spNature communications · 2026
    Article
  3. CYP3A Mediates an Unusual C(spAngewandte Chemie (International ed. in English) · 2024
    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.

Jun ZhuDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Yibin XueDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Rui ZhangDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Benjamin L RatchfordDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Guangbin DongDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.ORCID 0000-0003-1331-6015

Funding

Catalytic C-C Activation of Ketones - Renewal 01R01GM109054 · NIGMS · UNIVERSITY OF TEXAS AT AUSTIN · PI DONG, GUANGBIN · 2013 to 2025
$3.9M
NIGMS NIH HHS R01 GM109054
6 · The paper itself

Abstract

Catalytic activation of unstrained and nonpolar C-C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained C(aryl)-C(alkyl) bonds in 2,2'-methylenediphenols aided by removable directing groups. Good yields of the monophenol products are obtained with tolerating a wide range of functional groups. In addition, the reaction is scalable, and the catalyst loading can be reduced to as low as 0.5 mol %. Moreover, this method proves to be effective to cleave C(aryl)-C(alkyl) linkages in both models of phenolic resins and commercial novolacs resins. Finally, detailed experimental and computational mechanistic studies show that with C-H activation being a competitive but reversible off-cycle reaction, this transformation goes through a directed C(aryl)-C(alkyl) oxidative addition pathway.

Indexed as

Benzhydryl CompoundsCatalysisCoordination ComplexesHydrogenModels, ChemicalMolecular StructureOxidation-ReductionPhenolsRhodiumBenzhydryl CompoundsCoordination ComplexesHydrogenPhenolsRhodium

Identifiers

PMID35138096
PMCPMC9115852

What OpenQuestion holds

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Registered trials

None linked

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.