Evidence map›Paper›PMID 27338703›Full record

ArticleScience (New York, N.Y.)2016

Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.

Emily B Corcoran, Michael T Pirnot, Shishi Lin, Spencer D Dreher, Daniel A DiRocco, Ian W Davies, Stephen L Buchwald, David W C MacMillan

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 122 papers.

0numbers the graph read from it
0cells of the map it votes in
122citing papers in PubMed
48.7field-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

122 citing papers in PubMed, 615 citations in OpenAlex.

  1. Article
  2. Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Review
  5. Article
  6. Article
  7. Review
  8. Advances in NiACS catalysis · 2026
    Review
  9. Article
  10. Review
  11. Article
  12. Review
  13. Journal of the American Chemical Society · 2025
    Article
  14. Article
  15. Review
  16. Article
  17. Review
  18. Article
  19. Article
  20. Review

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

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

8 authors at 3 institutions in 1 country.

Emily B CorcoranMerck Center for Catalysis at Princeton University, Princeton, NJ 08544, USA.
Michael T PirnotDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Shishi LinDepartment of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA.
Spencer D DreherDepartment of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA.
Daniel A DiRoccoDepartment of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA.
Ian W DaviesDepartment of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. dmacmill@princeton.edu sbuchwal@mit.edu.
David W C MacMillanMerck Center for Catalysis at Princeton University, Princeton, NJ 08544, USA. dmacmill@princeton.edu sbuchwal@mit.edu.
Merck & Co., Inc., Rahway, NJ, USA (United States) · USMassachusetts Institute of Technology · USPrinceton University · US

Funding

LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
Photoredox Catalysis Applications in Organometallics and Chemical BiologyR01GM078201 · NIGMS · PRINCETON UNIVERSITY · PI MACMILLAN, DAVID W · 2006 to 2019
$3.9M
Asymmetric Construction of Benzylic Stereocenters via Reductive Copper CatalysisF32GM113311 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI PIRNOT, MICHAEL THOMAS · 2015 to 2017
$128k
NIGMS NIH HHS F32 GM113311NIGMS NIH HHS GM113311NIGMS NIH HHS GM58160NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R01 GM078201NIGMS NIH HHS R01-GM078201-05
6 · The paper itself

Abstract

Over the past two decades, there have been major developments in transition metal-catalyzed aminations of aryl halides to form anilines, a common structure found in drug agents, natural product isolates, and fine chemicals. Many of these approaches have enabled highly efficient and selective coupling through the design of specialized ligands, which facilitate reductive elimination from a destabilized metal center. We postulated that a general and complementary method for carbon-nitrogen bond formation could be developed through the destabilization of a metal amido complex via photoredox catalysis, thus providing an alternative approach to the use of structurally complex ligand systems. Here, we report the development of a distinct mechanistic paradigm for aryl amination using ligand-free nickel(II) salts, in which facile reductive elimination from the nickel metal center is induced via a photoredox-catalyzed electron-transfer event.

Identifiers

PMID27338703
PMCPMC5027643
OpenAlexW2474218053

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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.