Evidence map›Paper›PMID 37142571›Full record

ArticleNature communications2023

C(alkyl)-C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction.

Qingyang Zhao, Le Yu, Yao-Du Zhang, Yong-Qiang Guo, Ming Chen, Zhi-Hui Ren, Zheng-Hui Guan

Abstract read
In one paragraph

Article in Nature communications, 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

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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. Review
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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

7 authors.

Qingyang Zhao *Key Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.ORCID http://orcid.org/0000-0001-8259-4321
Le Yu *Key Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.
Yao-Du Zhang *Key Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.
Yong-Qiang GuoKey Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.
Ming ChenKey Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.
Zhi-Hui RenKey Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China.
Zheng-Hui GuanKey Laboratory of Synthetic and Nature Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, P.R. China. guanzhh@nwu.edu.cn.ORCID http://orcid.org/0000-0003-4901-5951

Funding

National Natural Science Foundation of China (National Science Foundation of China) 22171224
6 · The paper itself

Abstract

Activation and cleavage of carbon-carbon (C-C) bonds is a fundamental transformation in organic chemistry while inert C-C bonds cleavage remains a long-standing challenge. Retro-Diels-Alder (retro-DA) reaction is a well-known and important tool for C-C bonds cleavage but less been explored in methodology by contrast to other strategies. Herein, we report a selective C(alkyl)-C(vinyl) bond cleavage strategy realized through the transient directing group mediated retro-Diels-Alder reaction of a six-membered palladacycle, which is obtained from an in situ generated hydrazone and palladium hydride species. This unprecedented strategy exhibits good tolerances and thus offers new opportunities for late-stage modifications of complex molecules. DFT calculations revealed that an intriguing retro-Pd(IV)-Diels-Alder process is possibly involved in the catalytic cycle, thus bridging both Retro-Diels-Alder reaction and C-C bond cleavage. We anticipate that this strategy should prove instrumental for potential applications to achieve the modification of functional organic skeletons in synthetic chemistry and other fields involving in molecular editing.

Identifiers

PMID37142571
PMCPMC10160084

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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.