Evidence map›Paper›PMID 36772856›Full record

ArticleJournal of labelled compounds & radiopharmaceuticals2023

Highly selective catalytic transfer hydrodeuteration of cyclic alkenes.

Samuel J Hintzsche, Zoua Pa Vang, Emanuel Rivera Torres, Mykaela Podoski, Joseph R Clark

Open access · bronzeAbstract read
In one paragraph

Article in Journal of labelled compounds & radiopharmaceuticals, 2023. 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
0.5field-weighted citation impact, top 44% 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, 4 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 1 institution in 1 country.

Samuel J HintzscheDepartment of Chemistry, Marquette University, Milwaukee, Wisconsin, USA.
Zoua Pa VangDepartment of Chemistry, Marquette University, Milwaukee, Wisconsin, USA.
Emanuel Rivera TorresDepartment of Chemistry, Marquette University, Milwaukee, Wisconsin, USA.
Mykaela PodoskiDepartment of Chemistry, Marquette University, Milwaukee, Wisconsin, USA.
Joseph R ClarkDepartment of Chemistry, Marquette University, Milwaukee, Wisconsin, USA.ORCID 0000-0002-3081-5732
Marquette University · US

Funding

Molecular Rotational Resonance Spectroscopy Instrumentation for the Quantification and Characterization of EnantioisotopomersR35GM147441 · NIGMS · UNIVERSITY OF TENNESSEE KNOXVILLE · PI Joseph Clark · 2022 to 2026
$2.1M
NIGMS NIH HHS R35 GM147441NIGMS NIH HHS R35 GM147441-01
6 · The paper itself

Abstract

Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.

Indexed as

CycloparaffinsAlkenesCatalysisCopperDeuteriumHydrogenAlkenesCopperCycloparaffinsDeuteriumHydrogencopperdeuterationhydrodeuterationhydrogenationtransition metal catalysis

Identifiers

PMID36772856
PMCPMC10226366
OpenAlexW4320033150

What OpenQuestion holds

Textmetadata
LicenceTDM
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.