35132-20-8, (1R,2R)-1,2-Diphenylethane-1,2-diamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
trans-RuH(eta1-BH4)[(R)-tolbinap][(R,R)-dpen] was synthesized. First, trans-RuCl2[(R)-tolbinap][(R,R)-dpen] was synthesized. That is, [RuCl2(benzene)]2 (129 mg; 0.258 mmol) (made by Aldrich Inc.) and (R)-TolBINAP (373 mg; 0.55 mmol) (made by AZmax Co., Ltd.) were weighed and placed in a 50 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding DMF (9 mL) with a syringe, heating in an oil bath set to 100 C. was performed for 10 minutes under an argon atmosphere. After cooling the reaction solution to room temperature, (R, R)-DPEN (117 mg; 0.55 mmol) (made by Kankyo Kagaku Center Co., Ltd.) was added under an argon gas flow to the reddish-brown RuCl2[(R)-tolbinap](dmf)n solution, and stirring at 25 C. was performed for 3 hours. To a green-colored crude product obtained by distilling off the DMF under reduced pressure (1 mmHg), methylene chloride (10 mL) was added, and after dissolving as much of a yellow product as possible, a green impurity was removed by filtration. The yellow solution that was obtained by filtration whereafter concentrated to approximately 1 mL and then diethyl ether (5 mL) was added to precipitate solids. The solids obtained were separated by filtration and dried under reduced pressure(1 mmHg)to obtain trans-RuCl2[(R)-tolbinap][(R,R)-dpen] (340 mg; 0.32 mmol; yield: 58%) as a yellow powder. [TolBINAP] and [tolbinap] are abbreviations for 2,2′-bis(di-4-tolylphosphino)-1,1′-binaphthyl, ?DMF? and ?dmf? are abbreviations for N,N-dimethylformamide, and ?DPEN? and ?dpen? are abbreviations for 1,2-diphenylethylenediamine. [00030] The abovementioned trans-RuCl2[(R)-tolbinap] [(R,R)-dpen] (106.3 mg; 0.1 mmol) and sodium borohydride (94.6 mg; 2.5 mmol) (made by Nacalai Tesque, Inc.) were then weighed and placed in a 50 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding a 1:1 volume ratio mixed solvent of benzene/ethanol (4 mL) with a syringe, heating in an oil bath set to 65 C. was performed for 5 minutes under an argon atmosphere. The reaction solution was thereafter stirred for 30 minutes at room temperature. After then drying and solidifying the crude product by distilling off the solvent under reduced pressure (1 mmHg), benzene (6 mL) was added under an argon gas flow to dissolve as much of a yellow product as possible and then the excess sodium borohydride was eliminated by filtration by celite (0.5 g). A yellow filtrate thus obtained was concentrated to approximately 1 ml by depressurization (1 mm Hg) and hexane (6 mL) was then added under an argon gas flow. Yellow solids thus precipitated were separated by filtration through a glass filter and dried under reduced pressure (1 mmHg) to obtain trans-RuH(eta1-BH4)[(R)-tolbinap] [(R,R)-dpen] (76.0 mg; yield: 70%; see formula (3) below) as a yellow powder. Decomposition temperature: 164 C.; 1HNMR(400 MHZ, C6D6) delta-13.60(t, 1, J=22.4 Hz, RuH), -0.40(brs, 4, BH4), 1.45(s, 3, CH3), 1.55(s, 3, CH3), 1.62(s, 3, CH3), 1.63(s, 3, CH3), 1.95(dd, 1, J=7.2 and 8.4 Hz, NHH), 2.38(d, 1, J=8.2 Hz, NHH) ,3.65(dd, 1, J=7.9 and 11.2 Hz, CHNH2), 3.82-3.88(m, 2, 2 NHH), 4.00(ddd, 1, J=7.9, 8.4 and 11.6 Hz, CHNH2), 6.13-8.12(m, 38, aromatics) ;31PNMR(161.7 MHz, C6D6) delta71.2(d, J=41.4 Hz), 75.2(d, J=41.4 Hz);IR(toluene)2316(s), 1862(s), 1092(s), 1080(s)cm-1; ESI-MS m/z1007.26([M-H]+), theoretical value (C62H60BN2P2Ru): 1007.34. The powder obtained was then recrystallized from a THF/hexane mixed solvent of a volume ratio of approximately 1:5 to obtain yellow prismatic crystals, and these were used for X-ray crystallography.
35132-20-8, 35132-20-8 (1R,2R)-1,2-Diphenylethane-1,2-diamine 2724998, acatalyst-ligand compound, is more and more widely used in various fields.
Reference£º
Patent; Nagoya Industrial Science Research Institute; US6720439; (2004); B1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI