Evidence map›Paper›PMID 21999801›Full record

ArticleJournal of the American Chemical Society2011

Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides.

Thomas J Maimone, Phillip J Milner, Tom Kinzel, Yong Zhang, Michael K Takase, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.

0numbers the graph read from it
0cells of the map it votes in
35citing 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

35 citing papers in PubMed.

  1. Article
  2. Article
  3. Mechanism of the Aryl-F Bond-Forming Step from Bi(V) Fluorides.Journal of the American Chemical Society · 2022
    Article
  4. Article
  5. Article
  6. Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020
    Article
  7. Article
  8. Article
  9. Base-Promoted, Remote C-H Activation at a Cationic (ηJournal of the American Chemical Society · 2019
    Article
  10. Article
  11. Palladium-Mediated Arylation of Lysine in Unprotected Peptides.Angewandte Chemie (International ed. in English) · 2017
    Article
  12. The Evolution of PdAccounts of chemical research · 2016
    Article
  13. Article
  14. Article
  15. Palladium-Catalyzed Arylation of Fluoroalkylamines.Journal of the American Chemical Society · 2015
    Article
  16. Article
  17. Structure and Reactivity of [(L•Pd)Inorganica chimica acta · 2014
    Article
  18. Article
  19. Pd-catalyzed nucleophilic fluorination of aryl bromides.Journal of the American Chemical Society · 2014
    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

6 authors.

Thomas J MaimoneDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Phillip J Milner
Tom Kinzel
Yong Zhang
Michael K Takase
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
Shape Shifting Phosphines in Transition Metal CatalysisF32GM088931 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI MAIMONE, THOMAS JOHN · 2009 to 2012
$130k
NIGMS NIH HHS 1F32GM088931NIGMS NIH HHS F32 GM088931NIGMS NIH HHS GM46059NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R37 GM046059
6 · The paper itself

Abstract

A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C-F reductive elimination from a LPd(II)(aryl)F complex (L = t-BuBrettPhos or RockPhos) does not occur when the aryl group is electron rich. Evidence is presented that a modified phosphine, generated in situ, serves as the actual supporting ligand during catalysis with such substrates. A preliminary study of the reactivity of a LPd(II)(aryl)F complex based on this modified ligand is reported.

Indexed as

CatalysisHydrocarbons, FluorinatedMesylatesModels, MolecularMolecular StructureOrganometallic CompoundsPalladiumStereoisomerismHydrocarbons, FluorinatedMesylatesOrganometallic CompoundsPalladiumtrifluoromethanesulfonic acid

Identifiers

PMID21999801
PMCPMC3354724

What OpenQuestion holds

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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.