Evidence map›Paper›PMID 26413908›Full record

ArticleJournal of the American Chemical Society2015

A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.

Aaron C Sather, Hong Geun Lee, Valentina Y De La Rosa, Yang Yang, Peter Müller, Stephen L Buchwald

Open access · bronzeAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.

0numbers the graph read from it
0cells of the map it votes in
25citing papers in PubMed
5.9field-weighted citation impact, top 3% 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

25 citing papers in PubMed, 128 citations in OpenAlex.

  1. Direct Regioselective para-Fluorination via I(I)/I(III) Catalysis.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Review
  3. Article
  4. IPr*Chemistry (Weinheim an der Bergstrasse, Germany) · 2024
    Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Mechanism of the Aryl-F Bond-Forming Step from Bi(V) Fluorides.Journal of the American Chemical Society · 2022
    Article
  13. Article
  14. Nature catalysis · 2020
    Article
  15. Article
  16. Base-Promoted, Remote C-H Activation at a Cationic (ηJournal of the American Chemical Society · 2019
    Article
  17. Review
  18. Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis.Angewandte Chemie (International ed. in English) · 2018
    Article
  19. Article
  20. Review
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 at 2 institutions in 1 country.

Aaron C SatherDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Hong Geun LeeDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Valentina Y De La RosaDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Yang YangDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Peter MüllerDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Massachusetts Institute of Technology · USUniversity of Pittsburgh · US

Funding

EARLY TRANSITION METAL CATALYSTS IN ORGANIC SYNTHESISR01GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1992 to 2016
$5.4M
Redox Controlled Reductive Elimination from Palladium II ComplexesF32GM108092 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI SATHER, AARON CHRISTOPHER · 2014 to 2017
$159k
NIGMS NIH HHS 1F32GM108092-01A1NIGMS NIH HHS F32 GM108092NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R01GM46059
6 · The paper itself

Abstract

A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.

Indexed as

TemperatureBromidesCatalysisCrystallography, X-RayFluorineLigandsModels, MolecularPalladiumBromidesFluorineLigandsPalladium

Identifiers

PMID26413908
PMCPMC4721526
OpenAlexW2270162735

What OpenQuestion holds

Textmetadata
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.