Evidence map›Paper›PMID 37059692›Full record

ArticleAngewandte Chemie (International ed. in English)2023

A General and Practical Route to Functionalized Bicyclo[1.1.1]Pentane-Heteroaryls Enabled by Photocatalytic Multicomponent Heteroarylation of [1.1.1]Propellane.

Weichen Huang, Sebastian Keess, Gary A Molander

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Expanding the Frontier of Linear Drug Design: Cu-Catalyzed CAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  5. Article
  6. Review
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

3 authors.

Weichen HuangRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA.ORCID http://orcid.org/0000-0001-7598-7880
Sebastian KeessMedicinal Chemistry Department, Neuroscience Discovery Research, AbbVie Deutschland GmbH & Co. KG, 67061, Ludwigshafen, Germany.
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA.ORCID http://orcid.org/0000-0002-9114-5584

Funding

Accessing New Chemical Space via Organic SynthesisR35GM131680 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2019 to 2022
$2.4M
Computational Methods for Selective CatalysisR01GM087605 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KOZLOWSKI, MARISA C · 2010 to 2019
$2.4M
Targeting Nucleic Acid Junctions with Small MoleculesR01GM118510 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI CHENOWETH, DAVID MICHAEL · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM087605NIGMS NIH HHS R01 GM118510NIGMS NIH HHS R35 GM131680
6 · The paper itself

Abstract

1-Aryl-substituted bicyclo[1.1.1]pentanes (BCPs) are an important class of BCP derivatives with widespread application in drug development. Most syntheses of these materials require multiple chemical steps via BCP electrophiles or nucleophiles derived from [1.1.1]propellane. Although one-step, multicomponent radical cross-coupling reactions could provide a more sustainable and rapid route to access diverse heteroarylated BCPs, current approaches are limited to tertiary alkyl radicals, leading to a decrease in their practical value. In this study, a conceptually different approach enabled by a radical multicomponent heteroarylation of [1.1.1]propellane to access functionalized heteroarylated BCPs is described. Importantly, this protocol is compatible with primary-, secondary-, and tertiary aliphatic radicals, as well as various fluoroalkyl radical sources, thus enabling rapid library generation of sought-after BCP derivatives for drug development.

Indexed as

Bicyclo[1.1.1]PentanesHeteroarylationMulticomponent ReactionsPhotocatalysisPropellanes

Identifiers

PMID37059692
PMCPMC10247404

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.