Evidence map›Paper›PMID 34415757›Full record

ArticleJournal of the American Chemical Society2021

Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate.

Vincent M Kassel, Christopher M Hanneman, Connor P Delaney, Scott E Denmark

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 17 papers.

0numbers the graph read from it
0cells of the map it votes in
17citing papers in PubMed
5.0field-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

17 citing papers in PubMed, 63 citations in OpenAlex.

  1. Article
  2. Review
  3. Automated Iterative N─C and C─C Bond Formation.Angewandte Chemie (International ed. in English) · 2025
    Article
  4. Article
  5. "Naked Nickel"-Catalyzed Heteroaryl-Heteroaryl Suzuki-Miyaura Coupling.Angewandte Chemie (International ed. in English) · 2025
    Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Review
  11. Article
  12. Article
  13. Article
  14. Chlorination of arenes via the degradation of toxic chlorophenols.Proceedings of the National Academy of Sciences of the United States of America · 2022
    Article
  15. Accounts of chemical research · 2022
    Article
  16. Article
  17. 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

4 authors at 1 institution in 1 country.

Vincent M KasselRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Christopher M HannemanRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Connor P DelaneyRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Scott E DenmarkRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.ORCID 0000-0002-1099-9765
University of Illinois Urbana-Champaign · US

Funding

Synthetic and Mechanistic Studies on Preparatively Significant ReactionsR35GM127010 · NIGMS · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2018 to 2022
$2.2M
NIGMS NIH HHS R35 GM127010
6 · The paper itself

Abstract

Reaction conditions have been developed for refractory heteroaryl-heteroaryl Suzuki-Miyaura cross-couplings. The reported method employs neopentyl heteroarylboronic esters as nucleophiles, heteroaryl bromides and chlorides as the electrophiles, and the soluble base potassium trimethylsilanolate (TMSOK) under anhydrous conditions. The addition of trimethyl borate enhances reaction rates by several mechanisms, including (1) solubilization of

Indexed as

BoratesBromidesCatalysisChloridesHeterocyclic CompoundsLigandsPalladiumSolubilityTrimethylsilyl CompoundsBoratesBromidesChloridesHeterocyclic CompoundsLigandsPalladiumpotassium trimethylsilanolatetrimethyl borateTrimethylsilyl Compounds

Identifiers

PMID34415757
PMCPMC8892994
OpenAlexW3194498405

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.