A kind of alkyl free radical and preparation method thereof
A free radical and alkyl technology, applied in the field of preparation of alkyl radicals, can solve the problems of too harsh reaction conditions and weak functional group tolerance
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Embodiment 1
[0033] Add benzyltrifluoroborate potassium salt (19.8mg, 0.1mmol, 1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6-tetrafluoroborate in sequence to a dry 10mL reaction tube Methyl piperidine oxide (15.6mg, 0.1mmol, 1.0eq.), replace the nitrogen three times, inject 1.0mL toluene and 20.0μL distilled water into the reaction tube under the nitrogen flow environment, tighten the cap of the reaction tube, at room temperature Stir vigorously for 10 minutes, and the formation of a silver mirror can be clearly seen on the wall of the reaction tube. The reaction solution was first filtered with diatomaceous earth to remove metal residues, the filter cake was washed three times with ethyl acetate, the filtrates were combined, spin-dried to obtain 23.5 mg of a colorless oily liquid by column chromatography, and the yield was 95%.
[0034] 1 H NMR(400MHz, CDCl3)δ7.33(m,5H),4.82(s,2H),1.50(m,4H),1.33(m,2H),1.25(s,6H),1.15(s,6H) ;
[0035] 13 C NMR (100MHz, CDCl3) δ128.3, 127...
Embodiment 2
[0037] In a dry 10mL reaction tube, add potassium phenethyltrifluoroborate (21.2mg, 0.1mmol, 1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- Tetramethylpiperidine oxide (15.6mg, 0.1mmol, 1.0eq.), replace the nitrogen three times, inject 1.0mL toluene and 20.0μL distilled water into the reaction tube under the nitrogen flow environment, tighten the reaction tube cap, at room temperature Under vigorous stirring for 10 minutes, the formation of a silver mirror can be clearly seen on the wall of the reaction tube. The reaction solution was first filtered with diatomaceous earth to remove metal residues, the filter cake was washed three times with ethyl acetate, the filtrates were combined, spin-dried to obtain 25.3 mg of a colorless oily liquid by column chromatography, and the yield was 97%.
[0038] 1 H NMR (400MHz, CDCl 3 )δ7.18(m,5H),3.87(t,J=6.8Hz,2H),2.75(t,J=6.8Hz,2H),1.34(m,4H),1.24(m,2H),0.99( s,12H);
[0039] 13 C NMR (100MHz, CDCl 3 )δ138.6, 128.1, 12...
Embodiment 3
[0041] In a dry 10mL reaction tube, add potassium phenylpropyltrifluoroborate (22.6mg, 0.1mmol, 1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- Tetramethylpiperidine oxide (15.6mg, 0.1mmol, 1.0eq.), replace the nitrogen three times, inject 1.0mL toluene and 20.0μL distilled water into the reaction tube under the nitrogen flow environment, tighten the reaction tube cap, at room temperature Under vigorous stirring for 10 minutes, the formation of a silver mirror can be clearly seen on the wall of the reaction tube. The reaction solution was first filtered with diatomaceous earth to remove metal residues, the filter cake was washed three times with ethyl acetate, the filtrates were combined, spin-dried to obtain 26.1 mg of a colorless oily liquid by column chromatography, and the yield was 95%.
[0042] 1 H NMR (400MHz, CDCl 3 )δ7.20(t, J=7.1Hz, 2H), 7.14-7.08(m, 3H), 3.70(t, J=6.3Hz, 2H), 2.63(t, J=7.8Hz, 2H), 1.82- 1.75(m,2H),1.47(m,1H),1.37-1.35(m,4H),1.25-1.19...
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