173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To a suspension of SIMes¡¤HCl (906mg, 2.64mmol) in THF (30mL) was added dropwise a 1.6M solution of n-butyl lithium in hexanes (1.65mL, 2.64mmol) at-78C with stirring. After 10min, the suspension was allowed to warm to room temperature for additional 10min. The mixture was cooled again to-78C and then treated with a cooled THF solution (-78C) of mesitylcopper (504mg including 0.09 equivalents of toluene, determined by 1H NMR, 2.64mmol) by means of a cannula. The reaction mixture was allowed to warm to room temperature and stirred for further 18h. The solvents were removed under reduced pressure. The resulting solid residue was dried for 2h and then extracted with toluene (50mL). The suspension was filtered through Kieselgur and the filter cake was washed with small portions of toluene (5mL). The resulting solution was concentrated under reduced pressure to 15mL and then stored at-18C for 18h while large colorless crystals were forming. The mother liquor was decanted from the crystals that were subsequently washed with cold toluene (5mL) and dried in vacuo for 15h. The mother liquor was combined with the washing solution, concentrated to 5mL and stored at-18C for about 3 weeks. From this solution a second crop of colorless crystals was isolated. Combined yield: 1.032g (2.11mmol, 80%). Anal. Calcd for C30H37N2Cu: C, 73.66; H, 7.62; N, 5.73. Found: C, 72.87; H, 7.91; N, 5.72. 1H NMR (500.13MHz, C6D6): delta 2.12 (s, 6H, p-CH3, NHC), 2.15 (s, 6H, o-CH3, CuMes), 2.18 (s, 12H, o-CH3, NHC), 2.26 (s, 3H, p-CH3, CuMes), 3.05 (s, 4H, CH2), 6.76 (s, 4H, CH, NHC), 6.86 (s, 2H, CH, CuMes). 13C NMR (125.77MHz, C6D6): delta 18.1 (o-CH3, NHC), 21.0 (p-CH3, NHC), 21.6 (p-CH3, CuMes), 28.0 (o-CH3, CuMes), 50.4 (CH2), 124.5 (CH, CuMes), 129.6 (CH, NHC), 132.7 (C, CuMes), 136.0, 136.2, 138.2 (3¡ÁC, Mes, NHC), 147.2 (C, CuMes), 163.7 (C, CuMes), 207.1 (C, CN2, NHC). MS (ESI in THF): m/z (rel. intensity)=675 (100) [(NHC)2Cu]+, 857 (34) [(NHC)2Cu2Mes]+; MS (ESI in CH3CN): m/z (rel. intensity)=764 (63) [(NHC)2Cu2(CN)]+, 675 (80) [(NHC)2Cu]+, 410 (42) [(NHC)Cu(CH3CN)]+, 397 (100) [(NHC)Cu(CO)]+, 369 (8) [(NHC)Cu]+, 307 (11) [(Mes)2(C3H4N2)+1]+. IR (KBr, cm-1): 3003, 2949, 2916, 2855, 2729, 2706, 1775, 1742, 1730, 1609, 1589, 1487, 1474, 1439, 1375, 1317, 1306, 1298, 1263, 1215, 1173, 1161, 1032, 1013, 951, 914, 883, 851, 839, 754, 741, 733, 721, 706, 689, 615, 602, 588, 573, 550, 532, 502, 482, 465, 419.
173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various.
Reference£º
Article; Stollenz, Michael; Fischer, Stefan; Gehring, Henrike; Resch, Stefan G.; Dechert, Sebastian; Grosse, Christian; Meyer, Franc; Journal of Organometallic Chemistry; vol. 821; (2016); p. 106 – 111;,
Chiral Catalysts
Chiral catalysts – SlideShare