Triethylamine Tris-hydrofluoride [(C₂H₅)₃N·3HF]: A Highly Versatile Source of Fluoride Ion for the Halofluorination of Alkenes

4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

“…Bearing in mind the high polarization of the N-Cl bond in the molecule of triazole 3a it can be proposed that reaction with potassium fluoride occurs by formation of chlorine fluoride. A similar proposal has been suggested earlier when studying the reactions of N-halosuccinimide with hydrofluoride salts [13,14]. The reaction of chlorine fluoride with the starting triazole occurs with cleavage of the C-SO 2 Tol-p bond to form the sulfofluoride 7.…”

Synthesis of 3-fluoropyrrolidines and 3-fluoroazetidines

“…3HF). 12 The resulting bromofluorinated imines can be used to synthesize the corresponding 3-fluoroazetidines, as described above. 9,10 At first, it was tried to extend this strategy toward the synthesis of 3-alkyl-3-fluoropyrrolidines, using N-(diphenylmethylidene)-3-methyl-3-butenylamine 5 as starting material for the bromofluorination reaction (Scheme 1).…”

Synthesis of new ligands for targeting the S1P1 receptor

“…Yield: 36 mg (11%). Similar to a known procedure, 36 hexadec-1-ene (6.2 mL, 4.88 g, 20.0 mmol, 92 % purity) and triethylamine trishydrofluoride (10 mL, 50.0 mmol, 2.5 equiv) were dissolved in dichloromethane (40 mL) and N-iodosuccinimide (NIS) (4.95 g, 22.0 mmol, 1.1 equiv) in dichloromethane (40 mL) was added under stirring at 0°C. The mixture was stirred at rt overnight.…”

“…Yield: 206 mg (58%). 36.0 (dt, 2 J C,F = 20.8 Hz, C-6), 38.7 (dt, 2 J C,F = 19.8 Hz, C-4), 55.1 (s, C-2), 65.2 (t, C-1 or C-3), 65.6 (t, C-1 or C-3), 91.4 (dt, 1 J C,F = 165.1 Hz, C-5). 19 …”