Reaction SMILES: [CH3:1][C:2]1[C:7]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:6]([N+:18]([O-])=O)[CH:5]=[CH:4][CH:3]=1.O.NN.[H][H]>[Ni]>[CH3:14][C:13]1[C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[NH2:18])=[C:9]([NH2:15])[CH:10]=[CH:11][CH:12]=1
Reactant: Cc1cccc([N+](=O)[O-])c1-c1c(C)cccc1[N+](=O)[O-]
Reactant: [H][H]
Agent: [Ni]
Agent: NN
Solvent: O
Product: Cc1cccc(N)c1-c1c(C)cccc1N

Procedure:
More specifically, o-toluidine (2) is treated with acetic anhydride to acetylate the amino group to obtain N-acetyl-o-toluidine (3). The compound (3) is nitrated with nitric acid to obtain 2-acetylamino-3-nitrotoluene (4) which is then hydrolyzed with a hydrochloric acid aqueous solution to obtain 2-amino-3-nitrotoluene (5). The compound (5) is diazotized with sodium nitrite in the presence of sulfuric acid and then treated with a potassium iodide aqueous solution to obtain crude 2-iodo-3-nitrotoluene (6). The crude product is recrystallized from ethanol to obtain a pale yellow pure compound (6). The compound (6) is allowed to react with stirring at 200° C. for 10 hours in the presence of a copper powder, and the reaction mixture is extracted with benzene using a Soxhlet extractor to obtain 6,6'-dimethyl-2,2'-dinitro-1,1'-biphenyl (7). The compound (7) is hydrogenated in the presence of a Raney nickel W2 type catalyst using hydrazine hydrate as a hydrogen source to obtain crude 6,6'-dimethyl-2,2'-diamino-1,1'-biphenyl (8). After the catalyst is removed, the solvent is removed under reduced pressure to obtain a pale yellow pure compound (8). Subsequently, the compound (8) is dissolved in a 47% hydrobromic acid aqueous solution, and a sodium nitrite aqueous solution is slowly added dropwise thereto under ice-cooling (0° C.), followed by stirring at -5° to -3° C. for 2.5 hours. The resulting solution is added slowly to a separately prepared refluxing solution of cuprous bromide in a 47% hydrobromic acid aqueous solution. After the addition, the mixture is further heated at reflux for 2.5 hours. To the reaction mixture are added methylene chloride and water, the mixture is stirred, and an organic layer is concentrated to obtain a black crude crystal. The crystal is purified twice by means of column chromatography to obtain 6,6'-dimethyl-2,2'-dibromo-1,1'-biphenyl (9) as a white crystal. The compound (9) is dissolved in tetrahydrofuran, the solution is cooled to -78° C., and a hexane solution of t-butyllithium is slowly added dropwise to the cooled solution. After the addition, the temperature is elevated to -45° C., and the reaction is continued for an additional 4 hours. After again cooling to -78° C., a tetrahydrofuran solution of dicyclohexylphosphinic chloride (10) is added to the reaction mixture, followed by allowing to warm to room temperature by spontaneous temperature elevation. The resulting mixture is heated at reflux for 3 hours. The solvent is removed by distillation under reduced pressure, toluene is added to the residue, and the residue is washed successively with a 2N sodium hydroxide aqueous solution and water, followed by concentration. Recrystallization of the concentrate from acetone gives racemic 2,2'-bis(dicyclohexylphosphinyl)-6,6'-dimethyl-1,1'-biphenyl (11) as a white crystal. The racemic compound (11) is dissolved in a mixed solvent of ethyl acetate and chloroform under heating, and a hot ethyl acetate solution of (-)-dibenzoyltartaric acid is added thereto, followed by allowing to stand to precipitate. The precipitated crystal is repeatedly recrystallized until the crystal shows a constant optical rotation.