Oxidative Fluorination of Heteroatoms Enabled by Trichloroisocyanuric Acid and Potassium Fluoride.
Angew Chem Int Ed Engl
; 61(31): e202205088, 2022 08 01.
Article
en En
| MEDLINE
| ID: mdl-35580251
ABSTRACT
In synthetic method development, the most rewarding path is seldom a straight line. While our initial entry into pentafluorosulfanyl (SF5 ) chemistry did not go according to plan (due to inaccessibility of reagents such as SF5 Cl at the time), a "detour" led us to establish mild and inexpensive oxidative fluorination conditions that made aryl-SF5 compound synthesis more accessible. The method involved the use of potassium fluoride and trichloroisocyanuric acid (TCICA)-a common swimming pool disinfectant-as opposed to previously employed reagents such as F2 , XeF2 , HF, and Cl2 . Thereafter, curiosity led us to explore applications of TCICA/KF as a more general approach to the synthesis of fluorinated Group 15, 16, and 17 heteroatoms in organic scaffolds; this, in turn, prompted SC-XRD, VT-NMR, computational, and physical organic studies. Ultimately, it was discovered that TCICA/KF can be used to synthesize SF5 Cl, enabling SF5 chemistry in an unexpected way.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Halogenación
/
Fluoruros
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2022
Tipo del documento:
Article
País de afiliación:
Estados Unidos