Evidence map›Paper›PMID 35688769›Full record

ArticleAngewandte Chemie (International ed. in English)2022

Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings.

Daniel C Salgueiro, Benjamin K Chi, Ilia A Guzei, Pablo García-Reynaga, Daniel J Weix

Open access · hybridAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.

0numbers the graph read from it
0cells of the map it votes in
27citing papers in PubMed
7.2field-weighted citation impact, top 2% 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

27 citing papers in PubMed, 70 citations in OpenAlex.

  1. Article
  2. Article
  3. Nickel-Catalyzed Radical-Radical Cross-Coupling Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  4. Article
  5. Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026
    Article
  6. Article
  7. Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026
    Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Review
  14. Article
  15. Article
  16. Article
  17. Expanding the Frontier of Linear Drug Design: Cu-Catalyzed CAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  18. Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024
    Article
  19. PrimaryFaraday discussions · 2023
    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

5 authors at 2 institutions in 1 country.

Daniel C SalgueiroDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.ORCID 0000-0002-6162-3493
Benjamin K ChiDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.ORCID 0000-0001-5672-9827
Ilia A GuzeiDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.ORCID 0000-0003-1976-7386
Pablo García-ReynagaJanssen Research & Development, LLC, 3210, Merryfield Row, San Diego, CA 92121, USA.
Daniel J WeixDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.ORCID 0000-0002-9552-3378
University of Wisconsin–Madison · USJanssen (United States) · US

Funding

Reductive Coupling Reactions: Trading Organometallic Reagents for Organic HalidesR01GM097243 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI Daniel John Weix · 2011 to 2026
$5.6M
NIGMS NIH HHS R01 GM097243
6 · The paper itself

Abstract

Strained rings are increasingly important for the design of pharmaceutical candidates, but cross-coupling of strained rings remains challenging. An attractive, but underdeveloped, approach to diverse functionalized carbocyclic and heterocyclic frameworks containing all-carbon quaternary centers is the coupling of abundant strained-ring carboxylic acids with abundant aryl halides. Herein we disclose the development of a nickel-catalyzed cross-electrophile approach that couples a variety of strained ring N-hydroxyphthalimide (NHP) esters, derived from the carboxylic acid in one step, with various aryl and heteroaryl halides under reductive conditions. The chemistry is enabled by the discovery of methods to control NHP ester reactivity, by tuning the solvent or using modified NHP esters, and the discovery that

Indexed as

Carboxylic AcidsEstersCatalysisNickelOxidation-ReductionCarboxylic AcidsEstersNickelCross-CouplingNickel CatalysisQuaternary CentersRedox-Active EstersStrained Rings

Identifiers

PMID35688769
PMCPMC9378488
OpenAlexW4281700677

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.