Ortho sulfonamide substituted diaryl iodide compounds, preparation method and application thereof
A technology of diaryl iodide and compound is applied in the field of organic synthesis and preparation, which can solve problems such as hindering atom economy, and achieve the effects of wide application range of substrates, green and environmental protection process, and efficient and convenient preparation method.
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[0057] The preparation method of sulfonamide iodobenzene derivative III used in the embodiment of the present invention comprises the following steps:
[0058]
[0059] Dissolve 2-iodoaniline compound V, sulfonyl chloride VI, anhydride VII and 4-dimethylaminopyridine in a molar ratio of 1:1:1:1 in a suitable solvent, react at 25-50°C for 12 hours, and extract. The solvent was spin-dried to obtain the compound sulfonamide iodobenzene derivative shown in formula III.
[0060] The 2-iodoaniline compound V is selected from one of the following structures:
[0061]
[0062] The sulfonyl chloride VI is selected from one of the following structures:
[0063]
[0064] The acid anhydride VII is acetic anhydride.
[0065] The solvent is at least one of dichloromethane, toluene, tetrahydrofuran, acetonitrile and ethyl acetate.
Embodiment 1
[0067]
[0068] Dissolve sulfonamide iodobenzene derivative III-1 (4.5 mmoles, 1 equivalent), selective fluorine (1.3 equivalents), and trimethylsilyl acetate (2.6 equivalents) in 15 mL of acetonitrile, and react at 50°C After 24 hours, cool to room temperature, add potassium phenyltrifluoroborate IV-1 (1.0 equivalent), add trimethylsilyl trifluoromethanesulfonate (1.0 equivalent) after it dissolves, spin dry the solvent after 12 hours of reaction , adding diethyl ether and triturating to precipitate a solid, which was filtered to obtain the compound ortho-sulfonamide substituted diaryliodonium derivative I-1 (white solid, 2.17 g, yield 72%).
[0069] M.p.:181-182℃.
[0070] 1 H NMR (400MHz, DMSO) δ8.59(d, J=7.6Hz, 1H), 8.24(d, J=7.8Hz, 2H), 7.85(d, J=7.0Hz, 1H), 7.79(t, J =7.4Hz,1H),7.69(q,J=7.9Hz,2H),7.56(t,J=7.7Hz,2H),7.14(s,2H),2.59(s,6H),2.30(s,3H ),1.34(s,3H).
[0071] 13 C NMR (101MHz, DMSO) δ170.39, 144.35, 141.27, 139.17, 137.86, 135.74, 133.94, 133.66, 133.02...
Embodiment 2
[0075]
[0076] Dissolve sulfonamide iodobenzene derivative III-1 (4.5 mmoles, 1 equivalent), selective fluorine (1.3 equivalents), and trimethylsilyl acetate (2.6 equivalents) in 15 mL of acetonitrile, and react at 50°C After 24 hours, and then cooled to room temperature, potassium 4-methylphenyltrifluoroborate IV-2 (1.0 eq) was added, followed by trimethylsilyl triflate (1.0 eq) after it dissolved. After reacting for 12 hours, the solvent was spin-dried, diethyl ether was added to triturate the precipitated solid, and the compound ortho-sulfonamide substituted diaryliodonium derivative I-2 was obtained by filtration (white solid, 2.58 g, yield 84%).
[0077] M.p.:147-148℃.
[0078] 1 H NMR (400MHz, DMSO) δ8.55 (dd, J = 8.0, 1.1Hz, 1H), 8.12 (d, J = 8.3Hz, 2H), 7.83 (dd, J = 7.9, 1.5Hz, 1H), 7.78 (td, J=7.7,1.3Hz,1H),7.66(td,J=7.9,1.6Hz,1H),7.37(d,J=8.3Hz,2H),7.14(s,2H),2.59(s, 6H), 2.35(s,3H), 2.30(s,3H), 1.39(s,3H).
[0079] 13 C NMR (101MHz, DMSO) δ170.43, 144.35, ...
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