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1293-65-8 1,1′-Dibromoferrocene 72376387, airon-catalyst compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1293-65-8,1,1′-Dibromoferrocene,as a common compound, the synthetic route is as follows.,1293-65-8

Example 1; L11,1′ bis-[(Sp,Rc,SFe)(1-N,N- Dimethylamino)ethylferrocenyl)phenylphosphino] ferrocene L1To a solution of (R)-N, N-dimethyl-1-ferrocenylethylamine [(R)-Ugi’s amine] (3.09 g, 12 mmol) in Et2O (20 ml) was added 1.5 M t-BuLi solution in pentane(8.0 ml, 12.0 mmol) at -78 0C. After addition was completed, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to -78 0C again, and dichlorophenylphosphine (1.63 ml, 12.0 mmol) was added in one portion. After stirring for 20 min at -78 0C, the mixture was slowly warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to -78 0C again, and a suspension of 1 ,1′ dilithioferrocene [prepared from 1 ,1′ dibromoferrocene(1.72 g, 5.0 mmol) and 1.5 M t-BuLi solution in pentane (14.0 ml, 21.0 mmol) in Et2O (20 ml) at -78 0C] was added slowly via a cannula. The mixture was warmed to room temperature and allowed to stir for 12 h. The reaction was quenched by the addition of saturated NaHCO3 solution (20 ml). The organic EPO layer was separated and dried over MgSO4 and the solvent removed under reduced pressure. The filtrate was concentrated. The residue was purified by chromatography (SiO2, hexane-EtOAc-Et3N = 85:10:5) to afford an orange solid (3.88 g, 85%) as a mixture of 95% his-(Sp,Rc,SFe) title compound L1 and 5% (Rp, Rc, S Fe-S p, Rc, S Fe) meso compound. The meso compound can be removed by further careful purification using chromatography (SiO2, hexane- EtOAc-Et3N = 85:10:5). Orange/yellow crystalline solid m.p. 190-192 0C. [alpha]D = -427 (c=0.005 (g/ml), toluene); 1H NMR (CDCI3, 400.13 MHz): delta 1.14 (d,6H,J = 6.7 Hz), 1.50 (s, 12H); 3.43 (m; 2H); 3.83 (m, 2H); 3.87 (m, 2H); 4.01 (s, 10H), 4.09 (t, 2H, J = 2.4 Hz); 4.11 (m, 2H); 4.20 (m, 2H); 4.28 (m, 2H); 4.61 (m, 2H); 4.42 (d, 2H1 J = 5.3 Hz); 7.18 (m, 6H); 7.42(m, 4H) ppm. 13C NMR (CDCI3, 100.61 MHz): delta 38.28, 57.40 (d, J = 5.6 Hz); 67.02, 69.04 (d, J = 4.0 Hz); 69.16 (d, J = 51.6 Hz); 69.66, 71.60 (d, J = 4.8 Hz), 71.91 (d, J = 7.2 Hz), 72.18 (d, J = 5.6 Hz), 75.96 (d, J = 35.7 Hz), 79.96 (d, J = 6.4 Hz), 95.73 (d, J = 19.1 Hz), 127.32 (d, J = 7.9 Hz), 127.62, 133.12 (d, J = 21.4 Hz), 139.73 (d, J = 4.0 Hz). 31P NMR (CDCI3, 162 MHz): delta -34.88 (s). Found: C, 65.53; H, 5.92; N 3.01 Calculated for C50H54Fe3N2P2; C, 65.81 ; H, 5.97; N, 3.07. HRMS (1OeV, ES+): Calcd for C50H55Fe3N2P2 [M+H]+: 913.1889; Found: 913.1952. The label SP refers to S configuration at phosphorus, Rc refers to R configuration at carbon (or other auxiliary) and Spe refers to S configuration at the planar chiral element.

1293-65-8 1,1′-Dibromoferrocene 72376387, airon-catalyst compound, is more and more widely used in various.

Reference£º
Patent; PHOENIX CHEMICALS LTD.; WO2006/75177; (2006); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion