Evidence map›Paper›PMID 37653636›Full record

ArticleCurrent organic synthesis2024

Scale-up of Sodium Persulfate Mediated, Nitroxide Catalyzed Oxidative Functionalization Reactions.

Katrina E Doherty, Arturo L Sandoval, Fabrizio Politano, Mason L Witko, Chelsea M Schroeder, William P Brydon, Geoffrey P Wadey, Kristiane K Ohlhorst, Nicholas E Leadbeater

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Article in Current organic synthesis, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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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

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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

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0 citing papers in PubMed, 0 citations in OpenAlex.

No citing paper in PubMed yet.

4 · The record

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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 at 1 institution in 2 countries.

Katrina E DohertyDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Arturo L SandovalDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.ORCID 0000-0003-4175-8689
Fabrizio PolitanoDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Mason L WitkoDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Chelsea M SchroederDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
William P BrydonDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Geoffrey P WadeyDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Kristiane K OhlhorstDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.
Nicholas E LeadbeaterDepartment of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA.ORCID 0000-0003-1823-5417
University of Connecticut · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

backgroundOxidation is a valuable tool in preparative organic chemistry. Oxoammonium salts and nitroxides have proven valuable as reagents and catalysts in this endeavor.

objectiveThe objective of this study is to scale up the oxidative amidation, ester formation, and nitrile formation using nitroxide as an organocatalyst.

methodsOxidative functionalization reactions were scaled from the 1 mmol to the 1 mole level. Sodium persulfate was used as the primary oxidant, and a nitroxide was employed as a catalyst. The products of the reactions were isolated in analytically pure form by extraction with no need for column chromatography.

resultsThe oxidative amidation and esterification of aldehydes can be scaled up from 1 mmol to 1 mole effectively, with comparable product yields being obtained at each increment. This work shows that conditions developed on a small scale can be transferred to a larger scale without reoptimization. The oxidative functionalization of aldehydes to prepare nitriles is not amenable to direct scale-up due to the concomitant formation of significant quantities of the corresponding carboxylic acid, thereby compromising the product yield.

conclusionTwo of the three oxidative transformations studied here can be scaled up successfully from the 1 mmol to the 1 mole level.

Indexed as

amidesand catalyst.estersOxidative functionalizationoxoammonium cationsscale-up

Identifiers

PMID37653636
OpenAlexW4386346643

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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.