Evidence map›Paper›PMID 34846142›Full record

ArticleJournal of the American Chemical Society2021

Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

David J Charboneau, Haotian Huang, Emily L Barth, Cameron C Germe, Nilay Hazari, Brandon Q Mercado, Mycah R Uehling, Susan L Zultanski

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.

0numbers the graph read from it
0cells of the map it votes in
33citing papers in PubMed
4.8field-weighted citation impact, top 4% 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

33 citing papers in PubMed, 71 citations in OpenAlex.

  1. Article
  2. Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Arylhydrazines: Convenient Homogeneous Reductants for Scalable Cross-Coupling.Angewandte Chemie (International ed. in English) · 2026
    Article
  5. Article
  6. Article
  7. Angewandte Chemie (International ed. in English) · 2026
    Article
  8. Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026
    Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Cross-Electrophile Coupling to Form Sterically Hindered C(spJournal of the American Chemical Society · 2025
    Article
  16. Article
  17. Review
  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

8 authors at 2 institutions in 1 country.

David J CharboneauDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.
Haotian HuangDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.
Emily L BarthDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.
Cameron C GermeDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.
Nilay HazariDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.ORCID 0000-0001-8337-198X
Brandon Q MercadoDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States.
Mycah R UehlingDiscovery Chemistry, HTE and Lead Discovery Capabilities, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.
Susan L ZultanskiDepartment of Process Research and Development, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.
Yale University · USMerck & Co., Inc., Rahway, NJ, USA (United States) · US

Funding

Mechanistic Studies to Rationally Design Ni and Pd Catalysts for Cross-CouplingR01GM120162 · NIGMS · YALE UNIVERSITY · PI HAZARI, NILAY · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM120162
6 · The paper itself

Abstract

The syntheses of four new tunable homogeneous organic reductants based on a tetraaminoethylene scaffold are reported. The new reductants have enhanced air stability compared to current homogeneous reductants for metal-mediated reductive transformations, such as cross-electrophile coupling (XEC), and are solids at room temperature. In particular, the weakest reductant is indefinitely stable in air and has a reduction potential of -0.85 V versus ferrocene, which is significantly milder than conventional reductants used in XEC. All of the new reductants can facilitate C(sp

Indexed as

AlkenesAminesHeterocyclic Compounds, 1-RingMolecular StructureOxidation-ReductionReducing AgentsAlkenesAminesHeterocyclic Compounds, 1-RingReducing Agents

Identifiers

PMID34846142
PMCPMC8678384
OpenAlexW3217532695

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.