Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43929083" target="_blank" >RIV/60461373:22310/24:43929083 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/24:43929083

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc00087k" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc00087k</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4gc00087k" target="_blank" >10.1039/d4gc00087k</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent

Popis výsledku v původním jazyce

The drawbacks commonly observed in synthetic methods for alcohol oxidation often stem from the utilization of complex, toxic, hazardous, or waste-producing oxidants. When sensitive or complex substrates bearing several functional groups are to be transformed, the selectivity of oxidation becomes another significant challenge. Herein, a chemoselective and operationally simple catalyst-free and additive-free method is presented for the aerial oxidation of 1-phenylpropargyl and 1-phenylallyl alcohols to their corresponding ketones, requiring only a solvent and visible light irradiation. The crucial role of dimethylsulfoxide (DMSO) as the solvent lies in achieving high chemoselectivity. Singlet oxygen, whose formation is photosensitized by the substrate and the product, is captured by DMSO, thereby preventing the undesired over-oxidation that occurs in other solvents. The application of DMSO to protect the substrate against singlet oxygen represents a novel approach that is potentially applicable to other aerobic photocatalytic processes. © 2024 The Royal Society of Chemistry.

Název v anglickém jazyce

Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent

Popis výsledku anglicky

The drawbacks commonly observed in synthetic methods for alcohol oxidation often stem from the utilization of complex, toxic, hazardous, or waste-producing oxidants. When sensitive or complex substrates bearing several functional groups are to be transformed, the selectivity of oxidation becomes another significant challenge. Herein, a chemoselective and operationally simple catalyst-free and additive-free method is presented for the aerial oxidation of 1-phenylpropargyl and 1-phenylallyl alcohols to their corresponding ketones, requiring only a solvent and visible light irradiation. The crucial role of dimethylsulfoxide (DMSO) as the solvent lies in achieving high chemoselectivity. Singlet oxygen, whose formation is photosensitized by the substrate and the product, is captured by DMSO, thereby preventing the undesired over-oxidation that occurs in other solvents. The application of DMSO to protect the substrate against singlet oxygen represents a novel approach that is potentially applicable to other aerobic photocatalytic processes. © 2024 The Royal Society of Chemistry.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GF21-14200K" target="_blank" >GF21-14200K: Cílený návrh flavinů pro organickou fotokatalýzu</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

GREEN CHEMISTRY

ISSN

1463-9262

e-ISSN

—

Svazek periodika

26

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

4880-4887

Kód UT WoS článku

001190251000001

EID výsledku v databázi Scopus

2-s2.0-85191010196