Evidence map›Paper›PMID 29916711›Full record

ArticleJournal of the American Chemical Society2018

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover.

James P Phelan, Simon B Lang, Jordan S Compton, Christopher B Kelly, Ryan Dykstra, Osvaldo Gutierrez, Gary A Molander

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 57 papers.

0numbers the graph read from it
0cells of the map it votes in
57citing 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

57 citing papers in PubMed.

  1. Article
  2. Direct photoexcitation of borate complexes for radical generation: A platform from organic synthesis to chemical biology.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2026
    Review
  3. Article
  4. Article
  5. Article
  6. Methyl Radical Addition Reactions to C═X Double Bonds.The Journal of organic chemistry · 2025
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  13. Alkene Carboxy-Alkylation via COJournal of the American Chemical Society · 2024
    Article
  14. Article
  15. Article
  16. Radical Polarity.Journal of the American Chemical Society · 2024
    Article
  17. Reductive Cyclopropanation through Bismuth Photocatalysis.Journal of the American Chemical Society · 2024
    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

7 authors.

James P PhelanRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
Simon B LangRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.ORCID 0000-0001-5380-2996
Jordan S ComptonRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.ORCID 0000-0001-7099-3456
Christopher B KellyRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.ORCID 0000-0002-5530-8606
Ryan DykstraDepartment of Chemistry and Biochemistry , University of Maryland , College Park , Maryland 20742 , United States.
Osvaldo GutierrezDepartment of Chemistry and Biochemistry , University of Maryland , College Park , Maryland 20742 , United States.ORCID 0000-0001-8151-7519
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.ORCID 0000-0002-9114-5584

Funding

A Novel Mechanistic Paradigm for Cross-CouplingR01GM113878 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2015 to 2018
$1.5M
Non-Organometallic Partners as Radical Precursors for the Diversification of Dual Catalytic Cross-Coupling ProcessesF32GM117634 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KELLY, CHRISTOPHER B. · 2016 to 2018
$138k
Merging hydrogen atom transfer processes with photoredox/nickel dual catalysis for the selective functionalization of C(sp3)-H bondsF32GM125241 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI PHELAN, JAMES PATRICK · 2017 to 2018
$65k
NIGMS NIH HHS F32 GM117634NIGMS NIH HHS F32 GM125241NIGMS NIH HHS R01 GM113878
6 · The paper itself

Abstract

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3- exo- tet ring closure, a pathway consistent with experimental and computational data.

Indexed as

AlkenesAmmonium CompoundsCatalysisCyclizationCyclopropanesHalogenationIndicators and ReagentsLightMethylationOxidation-ReductionAlkenesAmmonium CompoundsCyclopropanesIndicators and Reagents

Identifiers

PMID29916711
PMCPMC6540794

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.