Evidence map›Paper›PMID 32119162›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Anna V Bay, Keegan P Fitzpatrick, Rick C Betori, Karl A Scheidt

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. 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
–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

43 citing papers in PubMed.

  1. Article
  2. Review
  3. Article
  4. Deconstructive Radical-Radical Coupling for Programmable Remote Acylation.Angewandte Chemie (International ed. in English) · 2025
    Article
  5. Photochemical reduction of acylimidazolium salts.Beilstein journal of organic chemistry · 2025
    Article
  6. Review
  7. Article
  8. Article
  9. Science advances · 2024
    Article
  10. Article
  11. Article
  12. Article
  13. Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.Angewandte Chemie (International ed. in English) · 2023
    Article
  14. Review
  15. Photoredox-Catalyzed Radical-Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023
    Article
  16. Article
  17. Ketones from aldehydes via alkyl C(spNature communications · 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

4 authors.

Anna V BayDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, IL, 60208, USA.ORCID 0000-0003-3604-8316
Keegan P FitzpatrickDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, IL, 60208, USA.
Rick C BetoriDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, IL, 60208, USA.
Karl A ScheidtDepartment of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, IL, 60208, USA.ORCID 0000-0003-4856-3569

Funding

Supplement to Carbene Catalysis Strategies for Organic SynthesisR01GM073072 · NIGMS · NORTHWESTERN UNIVERSITY · PI SCHEIDT, KARL A · 2006 to 2018
$4.0M
New Acid Catalysis Concepts for Asymmetric SynthesisR01GM131431 · NIGMS · NORTHWESTERN UNIVERSITY · PI SCHEIDT, KARL A · 2019 to 2019
$305k
NIGMS NIH HHS R01 GM073072NIGMS NIH HHS R01 GM131431
6 · The paper itself

Abstract

As a key element in the construction of complex organic scaffolds, the formation of C-C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C-C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical-radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.

Indexed as

Photochemical ProcessesCarboxylic AcidsCatalysisChemistry Techniques, SyntheticHeterocyclic CompoundsKetonesMethaneOxidation-ReductioncarbeneCarboxylic AcidsHeterocyclic CompoundsKetonesMethaneketonesN-heterocyclic carbenesphotochemistryradicalsreaction mechanisms

Identifiers

PMID32119162
PMCPMC7250732

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.