Evidence map›Paper›PMID 26828576›Full record

ArticleOrganic letters2016

Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones.

Javad Amani, Esmat Sodagar, Gary A Molander

Open access · greenAbstract read
In one paragraph

Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.

0numbers the graph read from it
0cells of the map it votes in
26citing papers in PubMed
16.7field-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

26 citing papers in PubMed, 111 citations in OpenAlex.

  1. Photoredox-Catalyzed Radical-Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023
    Article
  2. Article
  3. Article
  4. Article
  5. Benzylic C(spChemical science · 2021
    Article
  6. Stereoinduction in Metallaphotoredox Catalysis.Angewandte Chemie (International ed. in English) · 2021
    Review
  7. Article
  8. Review
  9. Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.Angewandte Chemie (International ed. in English) · 2019
    Article
  10. Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.Angewandte Chemie (International ed. in English) · 2019
    Review
  11. Article
  12. Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.Journal of the American Chemical Society · 2018
    Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Review
  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.

Javad AmaniRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Esmat SodagarRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
University of Pennsylvania · US

Funding

A Novel Mechanistic Paradigm for Cross-CouplingR01GM113878 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2015 to 2018
$1.5M
Novel Borazines: Syntheses and ElaborationR01GM111465 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2015 to 2018
$1.0M
NIGMS NIH HHS R01 GM111465NIGMS NIH HHS R01 GM113878
6 · The paper itself

Abstract

A visible-light, single-electron-transfer (SET), photoredox cross-coupling for the synthesis of α-alkoxyketones has been developed. In this method, various aliphatic and aromatic acyl chlorides were successfully coupled with structurally diverse potassium alkoxymethyltrifluoroborates, producing the corresponding α-alkoxyketones with high yields. In this operationally simple and mild cross-coupling protocol, the desired ketones are obtained in one step from bench stable starting materials by a bond connection that is unique to both alkylboron chemistry and photoredox/Ni catalysis.

Indexed as

Boron CompoundsCatalysisCombinatorial Chemistry TechniquesElectron TransportHydrocarbons, ChlorinatedKetonesLightMolecular StructurePotassiumBoron CompoundsHydrocarbons, ChlorinatedKetonesPotassium

Identifiers

PMID26828576
PMCPMC5290490
OpenAlexW2278700534

What OpenQuestion holds

Textmetadata
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.