Evidence map›Paper›PMID 26912852›Full record

ArticleScience (New York, N.Y.)2016

Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

Quirin M Kainz, Carson D Matier, Agnieszka Bartoszewicz, Susan L Zultanski, Jonas C Peters, Gregory C Fu

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 171 papers.

0numbers the graph read from it
0cells of the map it votes in
171citing 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

171 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Article
  6. Biocatalytic Radical C(spResearch square · 2026
    Article
  7. Article
  8. Article
  9. Harnessing COJournal of the American Chemical Society · 2026
    Article
  10. Article
  11. Article
  12. Bimolecular Homolytic Substitution (SACS central science · 2025
    Review
  13. Article
  14. Article
  15. Radical Strategy to the Boron-to-Copper Transmetalation Problem:Journal of the American Chemical Society · 2025
    Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article

111 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

6 authors.

Quirin M KainzDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.
Carson D MatierDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.
Agnieszka BartoszewiczDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.
Susan L ZultanskiDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.
Jonas C PetersDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.
Gregory C FuDivision of Chemistry and Chemical Engineering, California Institute of Technology (Caltech), Pasadena, CA 91125, USA.

Funding

PHOTOINDUCED, COPPER-CATALYZED SUBSTITUTION REACTIONS OF ALKYL ELECTROPHILES BY NITROGEN NUCLEOPHILESR01GM109194 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI FU, GREGORY C · 2014 to 2021
$3.7M
NIGMS NIH HHS R01 GM109194NIGMS NIH HHS R01-GM109194
6 · The paper itself

Abstract

Despite a well-developed and growing body of work in copper catalysis, the potential of copper to serve as a photocatalyst remains underexplored. Here we describe a photoinduced copper-catalyzed method for coupling readily available racemic tertiary alkyl chloride electrophiles with amines to generate fully substituted stereocenters with high enantioselectivity. The reaction proceeds at -40°C under excitation by a blue light-emitting diode and benefits from the use of a single, Earth-abundant transition metal acting as both the photocatalyst and the source of asymmetric induction. An enantioconvergent mechanism transforms the racemic starting material into a single product enantiomer.

Identifiers

PMID26912852
PMCPMC4770572

What Socratic 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 Socratic graph.