Sulfur (VI) Fluoride Exchange (SuFEx) via Glass–Assisted Organocatalysis DOI

Ismat Nawaz,

Mohamed S. Nawaz,

Rahman Shah Zaib Saleem

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Abstract An environmentally benign route for the synthesis of sulfonamides via Sulfur (VI) Fluoride Exchange (SuFEx) chemistry utilizing N ‐methylimidazole, that simultaneously act as a base, precatalyst, HF by‐product scavenger, well solvent, is described. This one‐step sulfonamide exhibits excellent reactivity toward highly electron‐deficient and less nucleophilic anilines aminopyridines while tolerating wide range functional groups. In addition to desired target, we also isolated an ionic salt sole side product from reaction mixture has been identified bis[1‐methyl‐1 H ‐imidazole‐3‐ium] hexafluorosilicate (IV). The glass surface vessel acting source silicon present in product. Formation facilitating consumption sulfonyl fluoride synthesis. Optimization under various conditions, isolation bis[1‐methyl‐1H‐imidazole‐3‐ium] (IV) salt, highlight crucial role ‐methylimidazole support glass‐assisted approach. Besides first example glass–assisted SuFEx catalyzed by organic bases, this offers alternative accessing protic hexafluorosilicate‐based molten salts without employing external HF. synthetic utility late‐stage functionalization demonstrated.

Language: Английский

Substituent effects and electron delocalization in five-membered N-heterocycles DOI Creative Commons
Paweł A. Wieczorkiewicz, Tadeusz M. Krygowski, Halina Szatyłowicz

et al.

Physical Chemistry Chemical Physics, Journal Year: 2024, Volume and Issue: 26(28), P. 19398 - 19410

Published: Jan. 1, 2024

Five-membered N-heterocycles are principal constituents of many compounds vital importance in various fields chemistry, biochemistry or pharmaceutical chemistry. For this reason, unequivocal identification structural factors determining electron donating/withdrawing properties specific groups attached to the heterocyclic moiety becomes an utmost need together with elucidation substitution-induced changes cyclic and noncyclic delocalization. Thus, quantum-chemical calculations were performed for pyrrole, imidazole, pyrazole, 1,2,3- 1,2,4-triazole, their C-substituted mono-derivatives (X = NO

Language: Английский

Citations

2
Sulfur (VI) Fluoride Exchange (SuFEx) via Glass–Assisted Organocatalysis DOI

Ismat Nawaz,

Mohamed S. Nawaz,

Rahman Shah Zaib Saleem

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Abstract An environmentally benign route for the synthesis of sulfonamides via Sulfur (VI) Fluoride Exchange (SuFEx) chemistry utilizing N ‐methylimidazole, that simultaneously act as a base, precatalyst, HF by‐product scavenger, well solvent, is described. This one‐step sulfonamide exhibits excellent reactivity toward highly electron‐deficient and less nucleophilic anilines aminopyridines while tolerating wide range functional groups. In addition to desired target, we also isolated an ionic salt sole side product from reaction mixture has been identified bis[1‐methyl‐1 H ‐imidazole‐3‐ium] hexafluorosilicate (IV). The glass surface vessel acting source silicon present in product. Formation facilitating consumption sulfonyl fluoride synthesis. Optimization under various conditions, isolation bis[1‐methyl‐1H‐imidazole‐3‐ium] (IV) salt, highlight crucial role ‐methylimidazole support glass‐assisted approach. Besides first example glass–assisted SuFEx catalyzed by organic bases, this offers alternative accessing protic hexafluorosilicate‐based molten salts without employing external HF. synthetic utility late‐stage functionalization demonstrated.

Language: Английский

Citations

0