Evidence map›Paper›PMID 30905151›Full record

ArticleJournal of the American Chemical Society2019

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.

Yu Kawamata, Julien C Vantourout, David P Hickey, Peng Bai, Longrui Chen, Qinglong Hou, Wenhua Qiao, Koushik Barman, Martin A Edwards, Alberto F Garrido-Castro and 14 more

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 96 papers.

0numbers the graph read from it
0cells of the map it votes in
96citing 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

96 citing papers in PubMed.

  1. Article
  2. Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026
    Article
  3. Review
  4. Article
  5. Review
  6. Article
  7. Review
  8. Review
  9. General and selective nickel-electrocatalyzed cross-electrophile C*(Proceedings of the National Academy of Sciences of the United States of America · 2026
    Article
  10. Advances in NiACS catalysis · 2026
    Review
  11. Review
  12. Article
  13. Article
  14. Article
  15. Article
  16. Review
  17. Article
  18. Article
  19. Antioxidants: a comprehensive review.Archives of toxicology · 2025
    Review
  20. Evidence for a Unifying NiJournal of the American Chemical Society · 2025
    Article

36 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

24 authors.

Yu KawamataDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Julien C VantouroutDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0002-0602-069X
David P HickeyDepartment of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.ORCID 0000-0002-5297-6895
Peng BaiDepartment of Chemical Engineering and Materials Science , University of Minnesota , Minneapolis , Minnesota 55455 , United States.ORCID 0000-0002-6881-4663
Longrui ChenAsymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China.
Qinglong HouAsymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China.
Wenhua QiaoAsymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China.
Koushik BarmanDepartment of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.
Martin A EdwardsDepartment of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.ORCID 0000-0001-8072-361X
Alberto F Garrido-CastroDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0001-7262-7986
Justine N deGruyterDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0003-0465-8988
Hugh NakamuraDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Kyle KnouseDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0001-9688-0513
Chuanguang QinDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Khalyd J ClayDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Denghui BaoAsymchem Life Science (Tianjin) , Tianjin Economic-Technological Development Zone, Tianjin 300457 , China.
Chao LiDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0003-4529-5570
Jeremy T StarrDiscovery Sciences, Medicine Design , Pfizer Global Research and Development , 445 Eastern Point Road , Groton , Connecticut 06340 , United States.ORCID 0000-0001-8651-507X
Carmen Garcia-IrizarryDiscovery Sciences, Medicine Design , Pfizer Global Research and Development , 445 Eastern Point Road , Groton , Connecticut 06340 , United States.
Neal SachDepartment of Chemistry , La Jolla Laboratories, Pfizer , 10770 Science Center Drive , San Diego , California 92121 , United States.
Henry S WhiteDepartment of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.ORCID 0000-0002-5053-0996
Matthew NeurockDepartment of Chemical Engineering and Materials Science , University of Minnesota , Minneapolis , Minnesota 55455 , United States.
Shelley D MinteerDepartment of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112 , United States.ORCID 0000-0002-5788-2249
Phil S BaranDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0001-9193-9053

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.

Indexed as

Electrochemical TechniquesAminationAminesCatalysisDensity Functional TheoryKineticsMolecular StructureAmines

Identifiers

PMID30905151
PMCPMC6996791

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.