Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides.

Diazonium salts Electron transfer Photocatalyst Sulfonyl fluorides

Journal

Tetrahedron
ISSN: 0040-4020
Titre abrégé: Tetrahedron
Pays: England
ID NLM: 2984170R

Informations de publication

Date de publication:
12 Jun 2023
Historique:
pmc-release: 12 06 2024
medline: 26 2 2024
pubmed: 26 2 2024
entrez: 26 2 2024
Statut: ppublish

Résumé

Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.

Identifiants

pubmed: 38404686
doi: 10.1016/j.tet.2023.133364
pmc: PMC10887421
pii:
doi:

Types de publication

Journal Article

Langues

eng

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Cooper A Vincent (CA)

Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX, 75390-9038, United States.

Alexia Ripak (A)

Université Catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348, Louvain-la-Neuve, Belgium.

Ludovic Troian-Gautier (L)

Université Catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348, Louvain-la-Neuve, Belgium.

Uttam K Tambar (UK)

Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX, 75390-9038, United States.

Classifications MeSH