Evidence map›Paper›PMID 33215804›Full record

ArticleAngewandte Chemie (International ed. in English)2021

A Bidentate Iodine(III)-Based Halogen-Bond Donor as a Powerful Organocatalyst*.

Flemming Heinen, Dominik L Reinhard, Elric Engelage, Stefan M Huber

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.

0numbers the graph read from it
0cells of the map it votes in
24citing 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

24 citing papers in PubMed.

  1. Article
  2. Article
  3. Investigation of olefins as a cocatalyst for halonium catalysis.Chemical communications (Cambridge, England) · 2026
    Article
  4. Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025
    Article
  5. Asymmetric Counteranion-Directed Halogen Bonding Catalysis.Journal of the American Chemical Society · 2025
    Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Cyclic Homo- and Heterohalogen Di-λJournal of the American Chemical Society · 2023
    Article
  11. ηChemistry, an Asian journal · 2023
    Article
  12. Review
  13. Chiral Bromonium Salt (Hypervalent Bromine(III)) withMolecules (Basel, Switzerland) · 2023
    Article
  14. Synthesis and reactivity of azole-based iodazinium salts.Beilstein journal of organic chemistry · 2023
    Article
  15. Review
  16. Article
  17. Article
  18. Article
  19. Article
  20. Review
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

4 authors.

Flemming HeinenFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.
Dominik L ReinhardFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.
Elric EngelageFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.
Stefan M HuberFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.ORCID http://orcid.org/0000-0002-4125-159X

Funding

Deutsche Forschungsgemeinschaft EXC 2033Verband der Chemischen Industrie Dozentenstipendium
6 · The paper itself

Abstract

In contrast to iodine(I)-based halogen bond donors, iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels-Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF

Indexed as

Diels-Alder cycloadditionhalogen bondinghypervalent iodinenoncovalent interactionsorganocatalysis

Identifiers

PMID33215804
PMCPMC7986438

What OpenQuestion holds

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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.