Evidence map›Paper›PMID 35617373›Full record

ArticleScience (New York, N.Y.)2022

Catalyst-controlled site-selective methylene C-H lactonization of dicarboxylic acids.

Hau Sun Sam Chan, Ji-Min Yang, Jin-Quan Yu

Open access · greenAbstract read
In one paragraph

Article in Science (New York, N.Y.), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.

0numbers the graph read from it
0cells of the map it votes in
34citing papers in PubMed
15.7field-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

34 citing papers in PubMed, 95 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Review
  6. From Mono-Accounts of chemical research · 2025
    Review
  7. Transition-Metal-Catalyzed C(spTopics in current chemistry (Cham) · 2025
    Review
  8. Article
  9. Article
  10. Palladium-Catalyzed Methylene β-C-H Fluorination of Native Amides.Journal of the American Chemical Society · 2025
    Article
  11. Catalyst-Controlled Chemoselective γ-C(spJournal of the American Chemical Society · 2024
    Article
  12. Versatile Copper-Catalyzed γ-C(spJournal of the American Chemical Society · 2024
    Article
  13. Palladium-catalysed methylene C(Nature synthesis · 2024
    Article
  14. Review
  15. Article
  16. Ligand-Enabled γ-C(spJournal of the American Chemical Society · 2023
    Article
  17. Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023
    Article
  18. Article
  19. 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

3 authors at 1 institution in 1 country.

Hau Sun Sam Chan *Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0002-6307-4950
Ji-Min Yang *Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0002-0613-112X
Jin-Quan YuDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.ORCID 0000-0003-3560-5774
Scripps Research Institute · US

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

Catalyst-controlled site-selective activation of β- and γ-methylene carbon-hydrogen (C-H) bonds of free carboxylic acids is a long-standing challenge. Here we show that, with a pair of palladium catalysts assembled with quinoline-pyridone ligands of different chelate ring sizes, it is possible to perform highly site-selective monolactonization reactions with a wide range of dicarboxylic acids, generating structurally diverse and synthetically useful γ- and δ-lactones via site-selective β- or γ-methylene C-H activation. The remaining carboxyl group serves as a versatile linchpin for further synthetic applications, as demonstrated by the total synthesis of two natural products, myrotheciumone A and pedicellosine, from abundant dicarboxylic acids.

Identifiers

PMID35617373
PMCPMC10243502
OpenAlexW4281551743

What OpenQuestion holds

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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.