Evidence map›Paper›PMID 37800120›Full record

ArticleACS catalysis2023

Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross-Coupling of Alkynes with Alkyl Iodides.

Xiaojun Zeng, Chao Wang, Wenhao Yan, Jian Rong, Yanshan Song, Zhiwei Xiao, Aijie Cai, Steven H Liang, Wei Liu

Open access · greenAbstract read
In one paragraph

Article in ACS catalysis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing papers in PubMed
8.2field-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

5 citing papers in PubMed, 55 citations in OpenAlex.

  1. Article
  2. Harnessing COJournal of the American Chemical Society · 2026
    Article
  3. Article
  4. Expanding the Frontier of Linear Drug Design: Cu-Catalyzed CAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  5. 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

9 authors at 3 institutions in 2 countries.

Xiaojun ZengSchool of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China.ORCID 0000-0002-9425-4882
Chao WangDepartment of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.
Wenhao YanDepartment of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.
Jian RongDepartment of Radiology and Imaging Sciences, Emory University, Atlanta, Georgia 30322, United States.ORCID 0000-0002-3960-1669
Yanshan SongSchool of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China.
Zhiwei XiaoDepartment of Radiology and Imaging Sciences, Emory University, Atlanta, Georgia 30322, United States.
Aijie CaiDepartment of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.
Steven H LiangDepartment of Radiology and Imaging Sciences, Emory University, Atlanta, Georgia 30322, United States.ORCID 0000-0003-1413-6315
Wei LiuDepartment of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.ORCID 0000-0001-6249-3179
University of Cincinnati · USEmory University · USNanchang University · CN

Funding

PET ligand discovery for arginine vasopressinR01MH128705 · NIMH · EMORY UNIVERSITY · PI Steven H Liang · 2022 to 2026
$5.8M
Supplement for Ligand discovery for delineating cholesterol homeostasis in the brainR01AG070060 · NIA · MASSACHUSETTS GENERAL HOSPITAL · PI LIANG, STEVEN H · 2021 to 2025
$4.2M
Subtype-selective NMDA ligands for Alzheimer's DiseaseR01AG075444 · NIA · EMORY UNIVERSITY · PI LIANG, STEVEN H · 2022 to 2025
$3.1M
AMPAR ligand discovery for Alzheimer's diseaseRF1AG073428 · NIA · MASSACHUSETTS GENERAL HOSPITAL · PI LIANG, STEVEN H · 2021 to 2021
$2.3M
Subtype-selective phosphodiesterase PET ligandsR01AG079956 · NIA · EMORY UNIVERSITY · PI LIANG, STEVEN H · 2023 to 2025
$2.3M
New Strategies for Copper-Catalyzed Cross-Coupling of Alkyl ElectrophilesR35GM146765 · NIGMS · VIRGINIA POLYTECHNIC INST AND ST UNIV · PI Wei Liu · 2022 to 2026
$2.0M
NIA NIH HHS R01 AG070060NIA NIH HHS R01 AG075444NIA NIH HHS R01 AG079956NIA NIH HHS RF1 AG073428NIGMS NIH HHS R35 GM146765NIMH NIH HHS R01 MH128705
6 · The paper itself

Abstract

Despite the success of Sonogashira coupling for the synthesis of arylalkynes and conjugated enynes, the engagement of unactivated alkyl halides in such reactions remains historically challenging. We report herein a strategy that merges Cu-catalyzed alkyne transfer with the aryl radical activation of carbon-halide bonds to enable a general approach for the coupling of alkyl iodides with terminal alkynes. This unprecedented Sonogashira-type cross-coupling reaction tolerates a broad range of functional groups and has been applied to the late-stage cross-coupling of densely functionalized pharmaceutical agents as well as the synthesis of positron emission tomography tracers.

Indexed as

alkynearyl radicalcopperhalogen abstractionSonogashira coupling

Identifiers

PMID37800120
PMCPMC10552849
OpenAlexW4319594409

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.