Evidence map›Paper›PMID 37006689›Full record

ArticleChemical science2023

Atroposelective brominations to access chiral biaryl scaffolds using high-valent Pd-catalysis.

Sif T Linde, Vasco Corti, Vibeke H Lauridsen, Johannes N Lamhauge, Karl Anker Jørgensen, Nomaan M Rezayee

Abstract read
In one paragraph

Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. 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.

Sif T LindeDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.ORCID https://orcid.org/0000-0002-3314-0072
Vasco CortiDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.
Vibeke H LauridsenDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.
Johannes N LamhaugeDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.ORCID https://orcid.org/0000-0002-9115-4528
Karl Anker JørgensenDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.ORCID https://orcid.org/0000-0002-3482-6236
Nomaan M RezayeeDepartment of Chemistry, Aarhus University DK-8000 Aarhus C Denmark nmr@chem.au.dk.ORCID https://orcid.org/0000-0002-9622-6324

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Compounds featuring atropisomerism are ubiquitous in natural products, therapeutics, advanced materials, and asymmetric synthesis. However, stereoselective preparation of these compounds presents many synthetic challenges. This article introduces streamlined access to a versatile chiral biaryl template through C-H halogenation reactions employing high-valent Pd catalysis in combination with chiral transient directing groups. This methodology is highly scalable, insensitive to moisture and air, and proceeds, in select cases, with Pd-loadings as low as 1 mol%. Chiral mono-brominated, dibrominated, and bromochloro biaryls are prepared in high yield and excellent stereoselectivity. These serve as remarkable building blocks bearing orthogonal synthetic handles for a gamut of reactions. Empirical studies elucidated regioselective C-H activation to be predicated on the oxidation state of Pd and diverging site-halogenation to result from cooperative effects of Pd and oxidant.

Identifiers

PMID37006689
PMCPMC10055696

What OpenQuestion holds

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LicenceCC BY-NC
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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.