. Author manuscript; available in PMC: 2018 Aug 24.

Published in final edited form as: ACS Chem Neurosci. 2017 Mar 27;8(7):1530–1542. doi: 10.1021/acschemneuro.7b00051

Table 1.

[¹⁸F]Fluorination of diaryliodonium salts (5, 11 and 21) under various conditions.

Entry	I⁺ Salt^a	¹⁸F-fluoride [¹⁸F]F⁻X⁺	Method	T (°C)	t (min)	Solvent^b	TEMPO & H₂O^b	Product	Yield (%)^c	n
1	5	[¹⁸F]F⁻K⁺	manual	150	10	MeCN	–	[¹⁸F]6	NR	2
2	5	[¹⁸F]F⁻K⁺	manual	150	10	DMF	–	[¹⁸F]6	3 ± 2	2
3	5	[¹⁸F]F⁻TBA⁺	manual	150	10	DMF	–	[¹⁸F]6	Trace	2
4	5	[¹⁸F]F⁻Cs⁺	manual	150	10	DMF	–	[¹⁸F]6	9 ± 2	2
5	5	[¹⁸F]F⁻Cs⁺	manual	150	5	DMF	+	[¹⁸F]6	51 ± 5	3
6	5	[¹⁸F]F⁻Cs⁺	manual	130	5	DMF	+	[¹⁸F]6	31 ± 5	3
7	5	[¹⁸F]F⁻Cs⁺	manual	120	5	DMF	+	[¹⁸F]6	28 ± 3	3
8	5	[¹⁸F]F⁻Cs⁺	manual	150	15	DMF	+	[¹⁸F]6	43 ± 5	2
9	5	[¹⁸F]F⁻Cs⁺	manual	150	25	DMF	+	[¹⁸F]6	30 ± 5	2
10	11	[¹⁸F]F⁻Cs⁺	manual	150	5	DMF	+	[¹⁸F]22	16 ± 5	5
11	11	[¹⁸F]F⁻Cs⁺	manual	150	15	DMF	+	[¹⁸F]22	11 ± 4	3
12	11	[¹⁸F]F⁻Cs⁺	automated	150	5	DMF	+	[¹⁸F]1	7.0 ± 3.5 ^d	13
13	21	[¹⁸F]F⁻Cs⁺	automated	150	5	DMF	+	[¹⁸F]2	8.0 ± 3.5 ^e	12

Amount of diaryliodonium salt precursor used was 4-6 mg.

Reaction solvent (MeCN or DMF; 500 μL) prepared without (−) or with (+) 1 mg TEMPO and 10 μL of H₂O.

Progress of the reaction and yields for manual reactions were analyzed by radio-TLC (developing solvent: ethylacetate/hexane = 30:70, vol/vol).

Yield of the isolated pure product [¹⁸F]1 by semipreparative column (Phenomenex Synergi 10μ Hydro-RP 80A, 250×10 mm) using HPLC (5% EtOH in 40 mM NH₄OAc buffer, λ=254 nm, 4.0 ml/min).

Yield of the isolated pure product [¹⁸F]2 by semipreparative column (Phenomenex Synergi 10μ Hydro-RP 80A, 250×10 mm) using HPLC (3.5% EtOH in 40 mM NH₄OAc buffer, λ=254 nm, 4.0 ml/min).