Evidence map›Paper›PMID 38937591›Full record

ArticleNature chemistry2024

Modular assembly of arenes, ethylene and heteroarenes for the synthesis of 1,2-arylheteroaryl ethanes.

Tao Liu, Talin Li, Zhi Yuan Tea, Chu Wang, Tianruo Shen, Zhexuan Lei, Xuebo Chen, Weigang Zhang, Jie Wu

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Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing 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

7 citing papers in PubMed.

  1. Article
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  7. Arylthianthrenium Salts for Triplet Energy Transfer Catalysis.Journal of the American Chemical Society · 2024
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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

9 authors.

Tao LiuDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore.ORCID http://orcid.org/0000-0001-8084-3953
Talin LiDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore.ORCID http://orcid.org/0009-0004-0972-4934
Zhi Yuan TeaDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore.
Chu WangCollege of Chemistry, Beijing Normal University, Beijing, People's Republic of China.
Tianruo ShenScience, Mathematics and Technology Cluster, Singapore University of Technology and Design, Singapore, Republic of Singapore.ORCID http://orcid.org/0000-0001-5417-0783
Zhexuan LeiDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore.ORCID http://orcid.org/0000-0003-4653-5185
Xuebo ChenCollege of Chemistry, Beijing Normal University, Beijing, People's Republic of China.ORCID http://orcid.org/0000-0002-9814-9908
Weigang ZhangDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore. wgzhang@nus.edu.sg.ORCID http://orcid.org/0009-0000-3617-916X
Jie WuDepartment of Chemistry, National University of Singapore, Singapore, Republic of Singapore. chmjie@nus.edu.sg.ORCID http://orcid.org/0000-0002-9865-180X

Funding

National Natural Science Foundation of China (National Science Foundation of China) 22071170, 22371200National Research Foundation Singapore (National Research Foundation-Prime Minister's office, Republic of Singapore) NRFCRP25-2020RS-0002
6 · The paper itself

Abstract

The 1,2-arylheteroaryl ethane motif stands as a privileged scaffold with promising implications in drug discovery. Conventional de novo syntheses of these molecules have relied heavily on pre-functionalized synthons, entailing harsh conditions and multi-step processes. Here, to address these limitations, we present a modular approach for the direct synthesis of 1,2-arylheteroaryl ethanes using feedstock chemicals, including ethylene, arenes and heteroarenes. We disclosed a photo triplet-energy-transfer-initiated radical cascade process, leveraging homolytic cleavage of C-S bonds in aryl sulfonium salts as the key step to access aryl radicals with excellent regioselectivity. This method allows for rapid structural diversification of bioactive molecules, showcasing excellent functional group tolerance and streamlining the synthesis of bioactive compounds and their derivatives. Furthermore, our approach can be extended to propylene, non-gaseous terminal alkenes and various other electrophilic radical precursors, including heteroaryl radicals, hydroxyl radicals, trifluoromethyl radicals and α-carbonyl alkyl radicals. This study highlights the significance of radical polarity matching in designing selective multi-component couplings.

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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.