Evidence map›Paper›PMID 25299957›Full record

ArticleJournal of the American Chemical Society2014

Studying regioisomer formation in the Pd-catalyzed fluorination of aryl triflates by deuterium labeling.

Phillip J Milner, Tom Kinzel, Yong Zhang, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing 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

9 citing papers in PubMed.

  1. Article
  2. Fluoroarene Separations in Metal-Organic Frameworks with Two Proximal MgJournal of the American Chemical Society · 2021
    Article
  3. Article
  4. Off-Cycle Processes in Pd-Catalyzed Cross-Coupling of Carboranes.Organic process research & development · 2019
    Article
  5. Article
  6. Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCFAngewandte Chemie (International ed. in English) · 2016
    Article
  7. The Evolution of PdAccounts of chemical research · 2016
    Article
  8. Article
  9. 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.

Phillip J MilnerDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Tom Kinzel
Yong Zhang
Stephen L Buchwald

Funding

CATALYTIC METHODS FOR ORGANIC SYNTHESISR37GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 2000 to 2009
$8.1M
EARLY TRANSITION METAL CATALYSTS IN ORGANIC SYNTHESISR01GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1992 to 2016
$5.4M
NIGMS NIH HHS GM46059NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R37 GM046059
6 · The paper itself

Abstract

Isotopic labeling has been used to determine that a portion of the desired product in the Pd-catalyzed fluorination of electron-rich, non-ortho-substituted aryl triflates results from direct C-F cross-coupling. In some cases, formation of a Pd-aryne intermediate is responsible for producing undesired regioisomers. The generation of the Pd-aryne intermediate occurs primarily via ortho-deprotonation of a L·Pd(Ar)OTf (L = biaryl monophosphine) species by CsF and thus competes directly with the transmetalation step of the catalytic cycle. Deuterium labeling studies were conducted with a variety of aryl triflates.

Indexed as

CatalysisDeuteriumFluorineIsotope LabelingPalladiumDeuteriumFluorinePalladium

Identifiers

PMID25299957
PMCPMC4227819

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.