Evidence map›Paper›PMID 32480129›Full record

ArticleiScience2020

Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.

Yang Zheng, Ping Dai, Dafang Gao, Kemiao Hong, Luyao Kou, Shanliang Dong, Jundie Hu, Lihua Qiu, Wenhao Hu, Xiaoguang Bao and 1 more

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

Article in iScience, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it
0cells of the map it votes in
0citing papers in PubMed
0.1field-weighted citation impact, top 63% 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

0 citing papers in PubMed, 2 citations in OpenAlex.

No citing paper in PubMed yet.

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

11 authors at 3 institutions in 1 country.

Yang ZhengKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.
Ping DaiKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.
Dafang GaoKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.
Kemiao HongGuangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
Luyao KouKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.
Shanliang DongGuangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
Jundie HuKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China; Institute of Materials Science and Devices, Suzhou University of Science and Technology, Suzhou 215003, China.
Lihua QiuKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.
Wenhao HuGuangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China. Electronic address: huwh9@mail.sysu.edu.cn.
Xiaoguang BaoKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China. Electronic address: xgbao@suda.edu.cn.
Xinfang XuKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China; Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China. Electronic address: xinfangxu@suda.edu.cn.
Soochow University · CNSun Yat-sen University · CNSuzhou University of Science and Technology · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

An unprecedented desaturation method via redox-neutral hydrogen transfer process has been disclosed under mild conditions for the selective formation of terminal alkene with alkyl diazo compounds and aza-o-QMs. The control experiments and DFT calculations suggest that the visible light was introduced as a key parameter to enhance the reactivity via a radical process in the formation of closed-shell cyclopropane intermediate, followed by a ring opening and redox-neutral hydrogen transfer process to give the desaturated product. The high regioselectivity in this transformation is enabled by the internal amino species as an ancillary group (AG) in the final olefin formation step. This method provides a missing link in the expeditious preparation of synthetically useful 2-allyl anilines with broad substrate generality. Further applications of these generated products in N-heterocycle construction, including 5- and 6-membered rings with structural diversity, have been tactfully explored, which highlight the potential in methodology development and drug discovery.

Indexed as

Chemical SynthesisMaterials ChemistryOrganic Chemistry

Identifiers

PMID32480129
PMCPMC7262561
OpenAlexW3025714948

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
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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.