Ruthenium, [N-[(1R,2R)/(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]

Ruthenium, [N-[(1R,2R)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η, 1-methyl-4-(1-methylethyl)benzene] [192139-92-7] C31H35ClN2O2RuS (MW 636.26) InChI = 1S/C21H20N2O2S.C10H14.ClH.Ru/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17;1-8(2)10-6-4-9(3)5-7-10;;/h2-15,20-22H,1H3;4-8H,1-3H3;1H;/q-2;;;+3/p-1/t20-,21-;;;/m0.../s1 InChIKey = SQSSVHPWHOMXOZ-XCPIVNJJSA-M Ruthenium, [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene] [192139-90-5] C31H35ClN2O2RuS (MW 636.26) InChI = 1S/C21H20N2O2S.C10H14.ClH.Ru/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17;1-8(2)10-6-4-9(3)5-7-10;;/h2-15,20-22H,1H3;4-8H,1-3H3;1H;/q-2;;;+3/p-1/t20-,21-;;;/m1.../s1 InChIKey = SQSSVHPWHOMXOZ-AGEKDOICSA-M (reagent mostly used as a catalyst in asymmetric transfer hydrogenation of ketones and imines) Alternative Name: RuCl(p-cymene)[(R,R)/(S,S)-Ts-DPEN], Noyori's catalyst. Physical Data: mp 215 °C; (R,R)-[α]20D−116°, c = 0.1 in chloroform; (S,S)-[α]20D +178°, c = 0.5 in chloroform. Solubility: soluble in most organic solvents; insoluble in H2O, hexane. Form Supplied in: yellow/orange solid. Preparative Methods: although it can be obtained from many chemical suppliers, Noyori's catalyst is very easily prepared by heating (1S,2S)- or (1R,2R)-(-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (commercially available) and [RuCl2(η6-p-cymene)2]2 in the presence of triethylamine in isopropanol at 80 °C. Precipitation of the crude product with water allows purification of the catalyst by a simple filtration.1 An alternative protocol, using potassium hydroxide in a water–dichloromethane mixture, leads to the formation of the 16e− purple complex by further elimination of HCl.2 Handling, Storage, and Precautions: it is stable to air and moisture; it is, however, sensitive to basic and acidic conditions. Recovered catalyst cannot be purified or recycled over silica gel.