Evidence map›Paper›PMID 39843889›Full record

ArticleNature communications2025

Deoxygenative photochemical alkylation of secondary amides enables a streamlined synthesis of substituted amines.

Antonio Pulcinella, Stefano Bonciolini, Robin Stuhr, Damiano Diprima, Minh Thao Tran, Magnus Johansson, Axel Jacobi von Wangelin, Timothy Noël

Abstract read
In one paragraph

Article in Nature communications, 2025. 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
–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

5 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Enantioselective radical chemistry: a bright future ahead.Beilstein journal of organic chemistry · 2025
    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.

Antonio Pulcinella *Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Amsterdam, The Netherlands.
Stefano Bonciolini *Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Amsterdam, The Netherlands.ORCID http://orcid.org/0000-0002-2239-2549
Robin StuhrFlow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Amsterdam, The Netherlands.ORCID http://orcid.org/0000-0001-5932-1747
Damiano DiprimaFlow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Amsterdam, The Netherlands.
Minh Thao TranJanssen Pharmaceutica NV, Beerse, Belgium.ORCID http://orcid.org/0009-0009-8047-9333
Magnus JohanssonMedicinal Chemistry, Research and Early Development, Cardiovascular, Renal and Metabolism (CVRM), BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden.ORCID http://orcid.org/0000-0002-0904-2835
Axel Jacobi von WangelinDepartment of Chemistry, University of Hamburg, Hamburg, Germany.
Timothy NoëlFlow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Amsterdam, The Netherlands. t.noel@uva.nl.ORCID http://orcid.org/0000-0002-3107-6927

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Secondary amines are vital functional groups in pharmaceuticals, agrochemicals, and natural products, necessitating efficient synthetic methods. Traditional approaches, including N-monoalkylation and reductive amination, suffer from limitations such as poor chemoselectivity and complexity. Herein, we present a streamlined deoxygenative photochemical alkylation of secondary amides, enabling the efficient synthesis of α-branched secondary amines. Our method leverages triflic anhydride-mediated semi-reduction of amides to imines, followed by a photochemical radical alkylation step. This approach broadens the synthetic utility of amides, facilitating late-stage modifications of drug-like molecules and the synthesis of saturated N-substituted heterocycles. The pivotal role of flow technology in developing a scalable and robust process underscores the practicality of this method, significantly expanding the organic chemist's toolbox for complex amine synthesis.

Identifiers

PMID39843889
PMCPMC11754598

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Registered trials

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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.