Evidence map›Paper›PMID 32110346›Full record

ArticleChemical science2019

Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles.

Jichao Chen, Shang Gao, Ming Chen

Erratum issuedAbstract read
In one paragraph

Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. 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

5 · Who and what money

Authors and funding

3 authors.

Jichao ChenDepartment of Chemistry and Biochemistry , Auburn University , Auburn , AL 36849 , USA . Email: mzc0102@auburn.edu.
Shang GaoDepartment of Chemistry and Biochemistry , Auburn University , Auburn , AL 36849 , USA . Email: mzc0102@auburn.edu.
Ming ChenDepartment of Chemistry and Biochemistry , Auburn University , Auburn , AL 36849 , USA . Email: mzc0102@auburn.edu.ORCID 0000-0002-9841-8274

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C-C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon-carbon bonds sequentially.

Identifiers

PMID32110346
PMCPMC7020789

What OpenQuestion holds

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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.