Evidence map›Paper›PMID 30860849›Full record

ArticleOrganic letters2019

Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles.

Loïc R E Pantaine, John A Milligan, Jennifer K Matsui, Christopher B Kelly, Gary A Molander

Abstract read
In one paragraph

Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing 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

19 citing papers in PubMed.

  1. Article
  2. Radical Sampling Enabled Saturated N-Heterocycle Cyclization.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Alkene Carboxy-Alkylation via COJournal of the American Chemical Society · 2024
    Article
  5. Review
  6. Article
  7. Article
  8. Recent Advances in the Green Synthesis of ActivePharmaceuticals (Basel, Switzerland) · 2023
    Review
  9. Article
  10. Article
  11. Accessing IllusiveOrganic letters · 2022
    Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Review
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

5 authors.

Loïc R E PantaineRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
John A MilliganRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
Jennifer K MatsuiRoy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.ORCID 0000-0003-0693-0404
Christopher B KellyDepartment of Chemistry , Virginia Commonwealth University , 1001 West Main Street , P.O. Box 842006, Richmond , Virginia 23284-9069 , United States.ORCID 0000-0002-5530-8606
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

Accessing New Chemical Space via Organic SynthesisR35GM131680 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2019 to 2022
$2.4M
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
NIGMS NIH HHS F32 GM117634NIGMS NIH HHS R01 GM113878NIGMS NIH HHS R35 GM131680
6 · The paper itself

Abstract

Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl radicals possessing pendant leaving groups engage imines in C-C bond formation, and subsequent reduction of the intermediate nitrogen-centered radical triggers anionic ring closure. With the aid of visible light irradiation, substituted pyrrolidines, piperidines, and azepanes can be prepared under mild, redox-neutral conditions.

Indexed as

CyclizationHeterocyclic CompoundsIminesLightMolecular StructureNitrogenOxidation-ReductionHeterocyclic CompoundsIminesNitrogen

Identifiers

PMID30860849
PMCPMC6452489

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.