Evidence map›Paper›PMID 33514937›Full record

ArticleNature chemistry2021

Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source.

Yong Ho Lee, Elliott H Denton, Bill Morandi

Abstract read
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In one paragraph

Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing 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

10 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. The Divergent Reactivity of Acid Chlorides Under Transition Metal Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024
    Review
  6. Article
  7. Article
  8. Article
  9. Fragmentation and reassembly.Nature chemistry · 2021
    Article
  10. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

3 authors.

Yong Ho LeeLaboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Zurich, Switzerland.ORCID http://orcid.org/0000-0002-9768-7560
Elliott H DentonLaboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Zurich, Switzerland.
Bill MorandiLaboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Zurich, Switzerland. bill.morandi@org.chem.ethz.ch.ORCID http://orcid.org/0000-0003-3968-1424

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Hydroformylation, a reaction that installs both a C-H bond and an aldehyde group across an unsaturated substrate, is one of the most important catalytic reactions in both industry and academia. Given the synthetic importance of creating new C-C bonds, the development of carboformylation reactions, wherein a new C-C bond is formed instead of a C-H bond, would bear enormous synthetic potential to rapidly increase molecular complexity in the synthesis of valuable aldehydes. However, the demanding complexity inherent in a four-component reaction, utilizing an exogenous CO source, has made the development of a direct carboformylation reaction a formidable challenge. Here, we describe a palladium-catalysed strategy that uses readily available aroyl chlorides as a carbon electrophile and CO source, in tandem with a sterically congested hydrosilane, to perform a stereoselective carboformylation of alkynes. An extension of this protocol to four chemodivergent carbonylations further highlights the creative opportunity offered by this strategy in carbonylation chemistry.

Identifiers

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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.