Evidence map›Paper›PMID 34840353›Full record

ArticleScience (New York, N.Y.)2021

A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen.

Zhen Li, Zhen Wang, Nikita Chekshin, Shaoqun Qian, Jennifer X Qiao, Peter T Cheng, Kap-Sun Yeung, William R Ewing, Jin-Quan Yu

Open access · greenAbstract read
In one paragraph

Article in Science (New York, N.Y.), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.

0numbers the graph read from it
0cells of the map it votes in
43citing papers in PubMed
9.7field-weighted citation impact, top 1% of its field
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

43 citing papers in PubMed, 165 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Review
  5. From Mono-Accounts of chemical research · 2025
    Review
  6. Article
  7. Total Synthesis of the Nominal Structure of (+)-Talaromyolide D.Journal of the American Chemical Society · 2025
    Article
  8. Article
  9. Article
  10. Direct Pd-Catalyzed β-C(spOrganic letters · 2025
    Article
  11. Article
  12. Article
  13. Article
  14. Review
  15. Direct C-H Hydroxylation ofJournal of the American Chemical Society · 2024
    Article
  16. Article
  17. Article
  18. Review
  19. Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023
    Article
  20. 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

9 authors at 3 institutions in 2 countries.

Zhen Li *The Scripps Research Institute, La Jolla, CA 92037, USA.
Zhen Wang *The Scripps Research Institute, La Jolla, CA 92037, USA.
Nikita ChekshinThe Scripps Research Institute, La Jolla, CA 92037, USA.
Shaoqun QianThe Scripps Research Institute, La Jolla, CA 92037, USA.
Jennifer X QiaoDiscovery Chemistry, Bristol-Myers Squibb, Princeton, NJ 08543, USA.
Peter T ChengDiscovery Chemistry, Bristol-Myers Squibb, Princeton, NJ 08543, USA.
Kap-Sun YeungBristol-Myers Squibb Research and Development, Cambridge, MA 02142, USA.
William R EwingDiscovery Chemistry, Bristol-Myers Squibb, Princeton, NJ 08543, USA.
Jin-Quan YuThe Scripps Research Institute, La Jolla, CA 92037, USA.
Scripps Research Institute · USBristol-Myers Squibb (Sweden) · SEBristol-Myers Squibb (United States) · US

Funding

Catalyst-Controlled Site-Selective C-H Functionalizations of Arenes and HeteroarenesR01GM102265 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI YU, JIN-QUAN · 2012 to 2023
$4.6M
NIGMS NIH HHS R01 GM102265
6 · The paper itself

Abstract

Hydroxylation of aryl carbon-hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon-hydrogen hydroxylation reaction. The conventional site selectivity dictated by heterocycles is overturned by this catalyst, thus allowing late-stage modification of compounds of pharmaceutical interest at previously inaccessible sites.

Indexed as

Acids, HeterocyclicCarbonCarboxylic AcidsCatalysisHydrogenHydrogen BondingHydroxylationLigandsModels, MolecularMolecular StructureOxygenPalladiumPyridinesPyridonesAcids, HeterocyclicCarbonCarboxylic AcidsHydrogenLigandsOxygenPalladiumpyridinePyridinesPyridones

Identifiers

PMID34840353
PMCPMC8622180
OpenAlexW3175526778

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

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.