Evidence map›Paper›PMID 39394263›Full record

ArticleNature chemistry2025

Triazenolysis of alkenes as an aza version of ozonolysis.

Aleksandr Koronatov, Pavel Sakharov, Deepak Ranolia, Alexander Kaushansky, Natalia Fridman, Mark Gandelman

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Article in Nature chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

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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

1 citing paper in PubMed.

  1. 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

6 authors.

Aleksandr KoronatovSchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel.ORCID http://orcid.org/0000-0002-5184-4890
Pavel SakharovSchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel.ORCID http://orcid.org/0000-0001-7746-7387
Deepak RanoliaSchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel.ORCID http://orcid.org/0000-0002-3018-2584
Alexander KaushanskySchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel.
Natalia FridmanSchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel.
Mark GandelmanSchulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Israel. chmark@technion.ac.il.ORCID http://orcid.org/0000-0002-9651-2902

Funding

Israel Science Foundation (ISF) 2000/23
6 · The paper itself

Abstract

Alkenes are broadly used in synthetic applications, thanks to their abundance and versatility. Ozonolysis is one of the most canonical transformations that converts alkenes into molecules bearing carbon-oxygen motifs via C=C bond cleavage. Despite its extensive use in both industrial and laboratory settings, the aza version-cleavage of alkenes to form carbon-nitrogen bonds-remains elusive. Here we report the conversion of alkenes into valuable amines via complete C=C bond disconnection. This process, which we have termed 'triazenolysis', is initiated by a (3 + 2) cycloaddition of triazadienium cation to an alkene. The triazolinium salt formed accepts hydride from borohydride anion and spontaneously decomposes to create new C-N motifs upon further reduction. The developed reaction is applicable to a broad range of cyclic alkenes to produce diamines, while various acyclic C=C bonds may be broken to generate two separate amine units. Computational analysis provides insights into the mechanism, including identification of the key step and elucidating the significance of Lewis acid catalysis.

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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.