Evidence map›Paper›PMID 31057986›Full record

ArticleACS catalysis2019

Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.

John E A Russell, Emily D Entz, Ian M Joyce, Sharon R Neufeldt

Abstract read
In one paragraph

Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Kinetic Analysis of Transmetalation at Prototypical NickelAngewandte Chemie (International ed. in English) · 2026
    Article
  2. The Versatile and StrategicChemical reviews · 2024
    Review
  3. 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.

John E A RussellDepartment of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Emily D EntzDepartment of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Ian M JoyceDepartment of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Sharon R NeufeldtDepartment of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.ORCID 0000-0001-7995-3995

Funding

Surveillance genome sequencing to detect SARS-CoV-2 virus variants in MontanaP20GM103546 · NIGMS · UNIVERSITY OF MONTANA · PI BOWLER, BRUCE E · 2012 to 2021
$19.2M
NIGMS NIH HHS P20 GM103546
6 · The paper itself

Abstract

Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl- heteroaryl, aryl-alkenyl, and aryl-alkynyl, using non-triflate phenol derivatives. A combination of experimental and computational studies implicate an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II)-chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.

Indexed as

cross-couplingDFTnickelphenol derivativestransmetalation

Identifiers

PMID31057986
PMCPMC6497415

What OpenQuestion holds

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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.