Evidence map›Paper›PMID 30067304›Full record

ArticleAngewandte Chemie (International ed. in English)2018

Metallaphotoredox Difluoromethylation of Aryl Bromides.

Vlad Bacauanu, Sébastien Cardinal, Motoshi Yamauchi, Masaru Kondo, David F Fernández, Richard Remy, David W C MacMillan

Open access · greenAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.

0numbers the graph read from it
0cells of the map it votes in
40citing papers in PubMed
9.5field-weighted citation impact, top 1% 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

40 citing papers in PubMed, 188 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Synthetic Strategies to Access Fluorinated Azoles.European journal of organic chemistry · 2025
    Article
  6. Review
  7. Highly Enantioselective Decarboxylative Difluoromethylation.Journal of the American Chemical Society · 2024
    Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Review
  15. Difluoroalkylation of Anilines via Photoinduced Methods.The Journal of organic chemistry · 2023
    Article
  16. Efficient Synthesis of 1Molecules (Basel, Switzerland) · 2023
    Article
  17. Article
  18. Article
  19. 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

7 authors at 1 institution in 1 country.

Vlad BacauanuMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.ORCID 0000-0003-3089-0692
Sébastien CardinalMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.
Motoshi YamauchiMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.
Masaru KondoMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.
David F FernándezMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.
Richard RemyMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.
David W C MacMillanMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.ORCID 0000-0001-6447-0587
Princeton University · US

Funding

Synergistic Catalysis for Chemical SynthesisR01GM103558 · NIGMS · PRINCETON UNIVERSITY · PI MACMILLAN, DAVID W · 2012 to 2019
$2.7M
NIGMS NIH HHS R01 GM103558NIGMS NIH HHS R01 GM103558-05Swiss National Science Foundation P2FRP2-178091
6 · The paper itself

Abstract

Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, a simple and commercially available alkyl halide, is harnessed as an effective source of difluoromethyl radical by silyl-radical-mediated halogen abstraction. The merger of this fluoroalkyl electrophile activation pathway with a dual nickel/photoredox catalytic platform enables the difluoromethylation of a diverse array of aryl and heteroaryl bromides under mild conditions. The utility of this procedure is showcased in the late-stage functionalization of several drug analogues.

Indexed as

LightBenzyl CompoundsBromidesCatalysisChlorofluorocarbons, MethaneDrug DesignNickelOxidation-ReductionBenzyl CompoundsBromidesChlorofluorocarbons, MethanefluoroformNickeldifluoromethylationfluorineheterocyclesnickelphotoredox catalysis

Identifiers

PMID30067304
PMCPMC6460465
OpenAlexW2887442072

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.