Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
18 03 2022
18 03 2022
Historique:
pubmed:
10
3
2022
medline:
21
4
2022
entrez:
9
3
2022
Statut:
ppublish
Résumé
A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.
Identifiants
pubmed: 35263540
doi: 10.1021/acs.orglett.2c00481
doi:
Substances chimiques
Carboxylic Acids
0
Protons
0
Sulfur Compounds
0
Dimethyl Sulfoxide
YOW8V9698H
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM