Evidence map›Paper›PMID 31090252›Full record

ArticleAngewandte Chemie (International ed. in English)2019

Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

Conghui Tang, Mikiko Okumura, Yunbo Zhu, Annie R Hooper, Yu Zhou, Yu-Hsuan Lee, David Sarlah

Open access · greenAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.

0numbers the graph read from it
0cells of the map it votes in
23citing papers in PubMed
2.8field-weighted citation impact, top 9% 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

23 citing papers in PubMed, 57 citations in OpenAlex.

  1. Article
  2. Chemical science · 2026
    Article
  3. Article
  4. Article
  5. Article
  6. Intermolecular Asymmetric Arylative Dearomatization of 1-Naphthols.Journal of the American Chemical Society · 2024
    Article
  7. Article
  8. Copper-Catalyzed Dearomative 1,2-Hydroamination.Angewandte Chemie (International ed. in English) · 2024
    Article
  9. Copper-Catalyzed DearomativeACS catalysis · 2024
    Article
  10. Review
  11. Article
  12. Article
  13. Review
  14. Article
  15. π-Extended Rubrenes via Dearomative Annulative π-Extension Reaction.Journal of the American Chemical Society · 2023
    Article
  16. Review
  17. Article
  18. Article
  19. Review
  20. 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

7 authors at 1 institution in 1 country.

Conghui TangRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Mikiko OkumuraRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Yunbo ZhuRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Annie R HooperRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Yu ZhouRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Yu-Hsuan LeeRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
David SarlahRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.ORCID 0000-0002-8736-8953
University of Illinois Urbana-Champaign · US

Funding

Dearomative Functionalization with ArenophilesR01GM122891 · NIGMS · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · PI SARLAH, DAVID · 2017 to 2025
$3.1M
American Chemical Society Petroleum Research Fund PRF#57175-DNI1NIGMS NIH HHS R01 GM122891NSF CHE-1654110
6 · The paper itself

Abstract

A protocol for palladium-catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one-pot method features a visible-light-mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium-catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn-1,4-selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.

Indexed as

Antidepressive AgentsCatalysisModels, MolecularMolecular StructureNaphthalenesPalladiumSertralineAntidepressive AgentsnaphthaleneNaphthalenesPalladiumSertralinearenesaromaticitycycloadditionspalladiumphotochemistry

Identifiers

PMID31090252
PMCPMC6640109
OpenAlexW2945061251

What OpenQuestion holds

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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.