Evidence map›Paper›PMID 33244009›Full record

ArticleNature communications2020

Empowering alcohols as carbonyl surrogates for Grignard-type reactions.

Chen-Chen Li, Haining Wang, Malcolm M Sim, Zihang Qiu, Zhang-Pei Chen, Rustam Z Khaliullin, Chao-Jun Li

Open access · goldAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Nature communications, 2020. 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
1.2field-weighted citation impact, top 23% of its field
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, 22 citations in OpenAlex.

  1. Article
  2. Article
  3. Pure and applied chemistry. Chimie pure et appliquee · 2023
    Article
  4. Article
  5. Catalytic Generation of Carbanions through Carbonyl Umpolung.Angewandte Chemie (International ed. in English) · 2021
    Review
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

7 authors at 1 institution in 1 country.

Chen-Chen LiDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.ORCID 0000-0002-3251-5450
Haining WangDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
Malcolm M SimDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
Zihang QiuDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.ORCID 0000-0002-8628-6497
Zhang-Pei ChenDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
Rustam Z KhaliullinDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
Chao-Jun LiDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada. cj.li@mcgill.ca.ORCID 0000-0002-3859-8824
Centre in Green Chemistry and Catalysis · CA

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The Grignard reaction is a fundamental tool for constructing C-C bonds. Although it is widely used in synthetic chemistry, it is normally applied in early stage functionalizations owing to poor functional group tolerance and less availability of carbonyls at late stages of molecular modifications. Herein, we report a Grignard-type reaction with alcohols as carbonyl surrogates by using a ruthenium(II) PNP-pincer complex as catalyst. This transformation proceeds via a carbonyl intermediate generated in situ from the dehydrogenation of alcohols, which is followed by a Grignard-type reaction with a hydrazone carbanion to form a C-C bond. The reaction conditions are mild and can tolerate a broad range of substrates. Moreover, no oxidant is involved during the entire transformation, with only H

Identifiers

PMID33244009
PMCPMC7691337
OpenAlexW3107131605

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

Registered trials

None linked

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.