Evidence map›Paper›PMID 37087477›Full record

ArticleNature communications2023

Nickel/biimidazole-catalyzed electrochemical enantioselective reductive cross-coupling of aryl aziridines with aryl iodides.

Yun-Zhao Wang, Zhen-Hua Wang, Inbal L Eshel, Bing Sun, Dong Liu, Yu-Cheng Gu, Anat Milo, Tian-Sheng Mei

Abstract read
In one paragraph

Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing 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

19 citing papers in PubMed.

  1. Article
  2. Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Dual Catalytic Enantioconvergent Carbamoylation of Aziridines.Journal of the American Chemical Society · 2025
    Article
  8. Review
  9. Article
  10. Review
  11. Article
  12. Article
  13. Article
  14. Ni-Catalyzed Asymmetric Reductive Arylation of α-Substituted Imides.Journal of the American Chemical Society · 2024
    Article
  15. Article
  16. Article
  17. β-Phenethylamine Synthesis: N-Pyridinium Aziridines as Latent Dual Electrophiles.Angewandte Chemie (International ed. in English) · 2024
    Article
  18. Article
  19. 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

8 authors.

Yun-Zhao Wang *State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, Shanghai, China.
Zhen-Hua Wang *State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, Shanghai, China.
Inbal L Eshel *Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, 841051, Israel.ORCID http://orcid.org/0000-0001-7839-1804
Bing SunState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, Shanghai, China.
Dong LiuState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, Shanghai, China.
Yu-Cheng GuSyngenta, Jealott's Hill International Research Centre, Berkshire, RE42 6EY, UK.ORCID http://orcid.org/0000-0002-6400-6167
Anat MiloDepartment of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, 841051, Israel. anatmilo@bgu.ac.il.ORCID http://orcid.org/0000-0003-1552-8193
Tian-Sheng MeiState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, Shanghai, China. mei7900@sioc.ac.cn.ORCID http://orcid.org/0000-0002-4985-1071

Funding

National Natural Science Foundation of China (National Science Foundation of China) 21772222National Natural Science Foundation of China (National Science Foundation of China) 21821002National Natural Science Foundation of China (National Science Foundation of China) 91956112Science and Technology Commission of Shanghai Municipality (Shanghai Municipal Science and Technology Commission) 18JC1415600Science and Technology Commission of Shanghai Municipality (Shanghai Municipal Science and Technology Commission) 20JC1417100
6 · The paper itself

Abstract

Here, we report an asymmetric electrochemical organonickel-catalyzed reductive cross-coupling of aryl aziridines with aryl iodides in an undivided cell, affording β-phenethylamines in good to excellent enantioselectivity with broad functional group tolerance. The combination of cyclic voltammetry analysis of the catalyst reduction potential as well as an electrode potential study provides a convenient route for reaction optimization. Overall, the high efficiency of this method is credited to the electroreduction-mediated turnover of the nickel catalyst instead of a metal reductant-mediated turnover. Mechanistic studies suggest a radical pathway is involved in the ring opening of aziridines. The statistical analysis serves to compare the different design requirements for photochemically and electrochemically mediated reactions under this type of mechanistic manifold.

Identifiers

PMID37087477
PMCPMC10122672

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