Evidence map›Paper›PMID 30154495›Full record

ArticleNature communications2018

Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

Xian Zhao, Hai-Yong Tu, Lei Guo, Shengqing Zhu, Feng-Ling Qing, Lingling Chu

Abstract read
In one paragraph

Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.

0numbers the graph read from it
0cells of the map it votes in
43citing 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

43 citing papers in PubMed.

  1. Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026
    Article
  2. Defluorinative Cyclization of Enamides with Fluoroalkyl Halides Through Two Vicinal C(spAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  3. Article
  4. Review
  5. The Divergent Reactivity of Acid Chlorides Under Transition Metal Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024
    Review
  6. Kinetics and Mechanism of PPhJournal of the American Chemical Society · 2024
    Article
  7. Regiodivergent Radical-Relay Alkene Dicarbofunctionalization.Journal of the American Chemical Society · 2024
    Article
  8. Article
  9. Article
  10. Article
  11. Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  12. Ketones from aldehydes via alkyl C(spNature communications · 2023
    Article
  13. Article
  14. Article
  15. Article
  16. Article
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  18. Article
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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.

Xian ZhaoState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China.
Hai-Yong TuState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China.
Lei GuoState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China.
Shengqing ZhuState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China.
Feng-Ling QingState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China.
Lingling ChuState Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, 201620, China. lingling.chu1@dhu.edu.cn.ORCID http://orcid.org/0000-0001-7969-0531

Funding

National Natural Science Foundation of China (National Science Foundation of China) 21702029
6 · The paper itself

Abstract

The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C-C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important β-fluoroalkyl ketones from simple starting materials.

Identifiers

PMID30154495
PMCPMC6113317

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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.