Evidence map›Paper›PMID 36697909›Full record

ArticleCommunications chemistry2022

Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade.

Chao Zhou, Andrey Shatskiy, Azamat Z Temerdashev, Markus D Kärkäs, Peter Dinér

Open access · goldAbstract read
In one paragraph

Article in Communications chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
3.1field-weighted citation impact, top 8% 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

1 citing paper in PubMed, 30 citations in OpenAlex.

  1. Article
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

5 authors at 2 institutions in 2 countries.

Chao ZhouDepartment of Chemistry, Division of Organic Chemistry, KTH Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.ORCID http://orcid.org/0000-0003-4942-8422
Andrey ShatskiyDepartment of Chemistry, Division of Organic Chemistry, KTH Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.ORCID http://orcid.org/0000-0002-7249-7437
Azamat Z TemerdashevDepartment of Analytical Chemistry, Kuban State University, Stavropolskaya St. 149, 350040, Krasnodar, Russia.ORCID http://orcid.org/0000-0002-8048-4740
Markus D KärkäsDepartment of Chemistry, Division of Organic Chemistry, KTH Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.ORCID http://orcid.org/0000-0002-6089-5454
Peter DinérDepartment of Chemistry, Division of Organic Chemistry, KTH Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden. diner@kth.se.ORCID http://orcid.org/0000-0001-6782-6622
KTH Royal Institute of Technology · SEKuban State University · RU

Funding

Ministry of Education and Science of the Russian Federation (Minobrnauka) FZEN-2020-0022Stiftelsen Olle Engkvist Byggmästare 204-0175Svenska Forskningsrådet Formas (Swedish Research Council Formas) 2019-01269Vetenskapsrådet (Swedish Research Council) 2020-04764Wenner-Gren Foundation (Wenner-Gren Foundation for Anthropological Research, Inc.) UPD2021-0145
6 · The paper itself

Abstract

Photo-mediated radical dearomatization involving 5-exo-trig cyclizations has proven to be an important route to accessing spirocyclic compounds, whereas 6-exo-trig spirocyclization has been much less explored. In this work, a dearomative annulation cascade is realized through photoredox-mediated C-O bond activation of aromatic carboxylic acids to produce two kinds of spirocyclic frameworks. Mechanistically, the acyl radical is formed through oxidation of triphenylphosphine and subsequent C-O bond cleavage, followed by a 6-exo-trig cyclization/SET/protonation sequence to generate the spiro-chromanone products in an intramolecular manner. Furthermore, the protocol was extended to more challenging intermolecular tandem sequences consisting of C-O bond cleavage, radical addition to an alkene substrate, and 5-exo-trig cyclization to yield complex spirocyclic lactams.

Identifiers

PMID36697909
PMCPMC9814605
OpenAlexW4290077688

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.