Evidence map›Paper›PMID 34762490›Full record

ArticleScience (New York, N.Y.)2021

Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C-H activation.

Zhen Wang, Liang Hu, Nikita Chekshin, Zhe Zhuang, Shaoqun Qian, Jennifer X Qiao, 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 49 papers.

0numbers the graph read from it
0cells of the map it votes in
49citing papers in PubMed
10.3field-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

49 citing papers in PubMed, 126 citations in OpenAlex.

  1. Ligand-Enabled Stereoselective Coupling of Methylene C(spAngewandte Chemie (International ed. in English) · 2026
    Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Article
  8. Review
  9. Article
  10. Article
  11. From Mono-Accounts of chemical research · 2025
    Review
  12. Transition-Metal-Catalyzed C(spTopics in current chemistry (Cham) · 2025
    Review
  13. Article
  14. Palladium-Catalyzed Methylene β-C-H Fluorination of Native Amides.Journal of the American Chemical Society · 2025
    Article
  15. Article
  16. Article
  17. Article
  18. Catalyst-Controlled Chemoselective γ-C(spJournal of the American Chemical Society · 2024
    Article
  19. Article
  20. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

7 authors at 2 institutions in 2 countries.

Zhen Wang *The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0001-8125-8019
Liang Hu *The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0002-2960-9560
Nikita ChekshinThe Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0002-9687-3310
Zhe ZhuangThe Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0001-6679-0496
Shaoqun QianThe Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.
Jennifer X QiaoDiscovery Chemistry, Bristol-Myers Squibb, P.O. Box 4000, Princeton, NJ 08543, USA.ORCID 0000-0002-6685-2092
Jin-Quan YuThe Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0003-3560-5774
Scripps Research Institute · USBristol-Myers Squibb (Sweden) · SE

Funding

Ligand-promoted Enantioselective C-H Activation ReactionsR01GM084019 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI YU, JIN-QUAN · 2008 to 2024
$9.5M
NIGMS NIH HHS R01 GM084019
6 · The paper itself

Abstract

Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine-pyridone ligands that enable divergent dehydrogenation reactions through palladium-catalyzed β-methylene C–H activation of carboxylic acids, leading to the direct syntheses of α,β-unsaturated carboxylic acids or γ-alkylidene butenolides. The directed nature of this pair of reactions allows chemoselective dehydrogenation of carboxylic acids in the presence of other enolizable functionalities such as ketones, providing chemoselectivity that is not possible by means of existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp

Indexed as

Chemistry Techniques, Synthetic4-ButyrolactoneCarbonCarboxylic AcidsCatalysisChemical PhenomenaHydrogenHydrogen BondingLigandsMolecular StructureOxidation-ReductionOxygenPalladiumPyridinesPyridones4-ButyrolactonebutenolideCarbonCarboxylic AcidsHydrogenLigandsOxygenPalladiumpyridinePyridinesPyridones

Identifiers

PMID34762490
PMCPMC9084903
OpenAlexW3213760854

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.