n-(4-indolyl)nitroheterocyclic carbene palladium complex and its application
A nitrogen-heterocyclic carbene and indolyl technology, applied in the fields of chemical synthesis and organometallic catalysis, can solve the problems of shortened catalyst life, difficult product purification, and low catalytic efficiency, and achieve catalytic cross-coupling reactions and high electron cloud density , the effect of improving stability
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Embodiment 1
[0026] Embodiment 1: the preparation of N-(4-indolyl) azacyclic carbene palladium complex a
[0027] With 3-(2-ethyl-1,3,5,7-tetramethyl-1H-indol-4-yl)-1-(2,6-diisopropylphenyl)-4,5- Dihydro-1H-imidazole-3-chloride (41 mg) was used as a raw material, and a magnetic stirrer, PdCl 2 (17mg), raw material (41mg), K 2 CO 3 (61mg) and pyridine (1mL), replace with argon and screw on the bottle stopper, stir overnight at 80°C, after the reaction is complete, cool to room temperature; add DCM to the reaction system to dilute, filter with diatomaceous earth, wash with DCM, and the filtrate After concentration, it was purified by silica gel column chromatography to obtain product a as a light yellow solid (34 mg, 56.2%);
[0028]
[0029] 1 H NMR (600MHz, CDCl 3 )δ8.40(d, J=5.1Hz, 2H), 7.40(t, J=7.6Hz, 1H), 7.33(t, J=7.7Hz, 1H), 7.31–7.25(m, 1H), 7.20– 7.19(m,1H),7.01–6.93(m,2H),6.73(s,1H),4.04–4.00(m,4H),3.90–3.87(m,1H),3.83(s,3H),3.35– 3.31(m,1H),2.73–2.64(m,5H),2.62(s,3H),2....
Embodiment 2
[0032] Embodiment 2: the preparation of N-(4-indolyl) azacyclic carbene palladium complex b
[0033] With 3-(2-ethyl-1,3,5,7-tetramethyl-1H-indol-4-yl)-1-m-tolyl-4,5-dihydro-1H-imidazole-3- Chloride (61mg) was used as a raw material, and a magnetic stirrer, PdCl 2 (28mg), raw material (61mg), K 2 CO 3 (99mg), 3-chloropyridine (1mL), replace with argon and screw on the bottle stopper, and stir overnight at 110°C; after the reaction is complete, cool to room temperature, add DCM to the reaction system to dilute, filter with diatomaceous earth, DCM washing. After the filtrate was concentrated, it was purified by silica gel column chromatography to obtain product b as a light yellow solid (42 mg, 43%);
[0034]
[0035] 1 H NMR (600MHz, CDCl 3 )δ8.41(d,J=2.3Hz,1H),8.32(dd,J=5.6,1.2Hz,1H),7.42(ddd,J=8.2,2.2,1.4Hz,1H),7.00–6.90(m ,3H),6.73(s,1H),4.22–4.01(m,3H),3.95–3.91(m,1H),3.85(s,3H),2.74–2.67(m,4H),2.67–2.60(m ,4H),2.56(s,3H),2.49(s,3H),2.47(s,3H),2.26(s,3H),1.10–1.0...
Embodiment 3
[0038] Embodiment 3: the preparation of N-(4-indolyl) azacyclic carbene palladium complex c
[0039] With 3-(2-ethyl-1,3,5,7-tetramethyl-1H-indol-4-yl)-1-(2,6-diisopropylphenyl)-4,5- Dihydro-1H-imidazole-3-chloride (58 mg) was used as a raw material, and a magnetic stirrer, PdCl 2 (24mg), raw material (58mg), K 2 CO 3 (86mg), 3-chloropyridine (1mL), replace with argon, screw on the bottle stopper, and stir overnight at 110°C. After the reaction is complete, cool to room temperature, add DCM to the reaction system to dilute, filter with diatomaceous earth, and wash with DCM; after the filtrate is concentrated, it is purified by silica gel column chromatography, and the obtained product c is a light yellow solid (44mg, 49% );
[0040]
[0041] 1 H NMR (600MHz, CDCl 3 )δ8.46(d, J=2.1Hz, 1H), 8.38(d, J=5.5Hz, 1H), 7.42(d, J=8.3Hz, 1H), 7.34(t, J=7.7Hz, 1H) ,7.27(d,J=7.6Hz,1H),7.20(d,J=1.0Hz,1H),6.93(dd,J=8.1,5.7Hz,1H),6.73(s,1H),4.03(dt, J=8.6,4.4Hz,4H), 3.87(d,J=6.6Hz,...
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