Evidence map›Paper›PMID 35432903›Full record

ArticleChemical science2022

α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.

Shengzu Duan, Yujin Zi, Lingling Wang, Jielun Cong, Wen Chen, Minyan Li, Hongbin Zhang, Xiaodong Yang, Patrick J Walsh

Abstract read
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In one paragraph

Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

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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

9 authors.

Shengzu DuanKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Yujin ZiKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Lingling WangKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Jielun CongKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Wen ChenKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-7782-3879
Minyan LiRoy and Diana Vagelos Laboratories Penn/Merck Laboratory for High-Throughput Experimentation Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia PA USA pwalsh@sas.upenn.edu liminyan@sas.upenn.edu.
Hongbin ZhangKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-2516-2634
Xiaodong YangKey Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Province Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-8466-5418
Patrick J WalshRoy and Diana Vagelos Laboratories Penn/Merck Laboratory for High-Throughput Experimentation Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia PA USA pwalsh@sas.upenn.edu liminyan@sas.upenn.edu.ORCID https://orcid.org/0000-0001-8392-4150

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

α-Branched amines are fundamental building blocks in a variety of natural products and pharmaceuticals. Herein is reported a unique cascade reaction that enables the preparation of α-branched amines bearing aryl or alkyl groups at the β- or γ-positions. The cascade is initiated by reduction of redox active esters to alkyl radicals. The resulting alkyl radicals are trapped by styrene derivatives, leading to benzylic radicals. The persistent 2-azaallyl radicals and benzylic radicals are proposed to undergo a radical-radical coupling leading to functionalized amine products. Evidence is provided that the role of the nickel catalyst is to promote formation of the alkyl radical from the redox active ester and not promote the C-C bond formation. The synthetic method introduced herein tolerates a variety of imines and redox active esters, allowing for efficient construction of amine building blocks.

Identifiers

PMID35432903
PMCPMC8966660

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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.