Novel synthetic method for imidazole onium salts
A synthetic method, the technology of imidazoles, applied in the field of chemical synthesis, can solve the problems of lack of industrial applicability, harsh reaction conditions, lengthy synthesis steps, etc., and achieve the effects of low cost, short reaction time and simple process
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Embodiment 1
[0021] Example 1: 1,3-Diphenyl- 1H -imidazolium-3-ium tetrafluoroborate ( Product 3a ) synthesis: substrate 1 is substituted imidazole derivative phenylimidazole (36 mg), substrate 2 is diaryliodonium non-nucleophilic anion salt diphenyliodonium tetrafluoroborate (138.0 mg), The feed ratio is 1: 1.5, and the catalyst is the copper salt Cu(OAc) of the IB group 2 ·H 2 O (2.5 mg), the dosage is 5 mol% equivalent (relative to the substrate 1 imidazole derivative phenylimidazole), and the solvent is an aprotic solvent N,N - Dimethylformamide (1 mL), add the above four reagents into the reactor, and react at 100 °C for 4 hours. After the reaction was completed, the solvent was removed, and purified by column chromatography to obtain an off-white solid with a yield of 97%. Proton NMR spectrum (deuterated dimethyl sulfoxide as solvent, Bruker AMX-400 NMR instrument) 1 H NMR (400 MHz, DMSO- d 6 ): δ 10.55 (s, 1H), 8.88 (s, 2H), 8.41 (d, J= 8.0 Hz, 4H), 8.09-8.18 (m, 6H). ...
Embodiment 2
[0022] Example 2: 1,3-bis(2-thienyl)imidazolium p-toluenesulfonate ( Product 3b ) synthesis: the implementation method is the same as in Example 1, the substrate 1 substituted imidazole derivative phenylimidazole is replaced by the substituted imidazole derivative 2-thiophene imidazole (37.5 mg), and the substrate 2 diaryliodonium non-nucleophilic The anionic salt diaryliodonium tetrafluoroborate was exchanged for the diheteroaryliodonium non-nucleophilic anionic salt bis(2-thienyl)iodonium p-toluenesulfonate (174 mg). Yield 86%. 1 H NMR (400 MHz, DMSO- d 6 ): δ 10.28 (s, 1H), 8.46 (s, 2H), 7.73 (d, J = 5.2 Hz, 2H), 7.64 (d, J = 2.8 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 7.20 (t, J = 4.0 Hz, 2H), 7.10 (d, J = 8.0 Hz, 2H), 2.29 (s, 3H). HRMS (ESI) [M-OTs - ] + Calculated value C 11 h 9 N 2 S 2 , 233.0202, test value, 233.0202.
Embodiment 3
[0023] Example 3: 1,3-Diphenyl-2-vinyl- 1H -imidazolium-3-ium tetrafluoroborate ( Product 3c ) synthesis: the implementation method is the same as in Example 1, except that the substrate 1 substituted imidazole derivative phenylimidazole is replaced by a substituted imidazole derivative 1-phenyl-2-vinyl- 1H - Imidazole (42.5 mg). The yield is 65%. 1 H NMR (400 MHz, DMSO- d 6 ): δ 8.89 (s, 2H), 8.42 (d, J = 8.0 Hz, 4H), 8.10-8.19 (m, 6H), 6.69 (dd, J = 17.3, 11.2 Hz, 1H), 6.24 (d, J = 17.3 Hz, 1H), 5.50 (d, J = 11.2 Hz, 1H). HRMS (ESI) ([M-BF 4 - ] + ) Calculated value C 17 h 15 N 2 , 247.1230, test value, 247.1232.
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