dicyclohexyl(1,1-diphenylprop-1-en-2-yl)phosphane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.358 g (2.20 mmol) of 3-bromothiophene and 4 mL of toluene under a nitrogen atmosphere. The bromothiophene was dissolved in the solvent. To this solution were added 0.343 g (2.03 mmol) of diphenylamine, 0.229 g (2.39 mmol) of sodium t-butoxide, 4.4 mg (1 mol % based on the amine) of palladium acetate, and 30.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 10 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.257 g (50%) of N-(3-thiophenyl)-N,N-diphenylamine. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.503 g (2.10 mmol) of p-tolyl triflate and 4 mL of dioxane under a nitrogen atmosphere. The triflate was dissolved in the solvent. To this solution were added 0.246 g (2.29 mmol) of p-toluidine, 0.658 g (3.10 mmol) of potassium phosphate, 19.9 mg (2.1 mol % based on the triflate) of tris(dibenzylideneacetone)dipalladium, and 58.7 mg (7.2 mmol % based on the triflate) of the 1,1-diphenyl-2(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 12 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.268 g (65%) of ditolylamine. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.275 g (2.00 mmol) of 4-chlorobenzonitrile and 4 mL of toluene under a nitrogen atmosphere. The nitrile was dissolved in the solvent. To this solution were added 0.192 g (2.2 mmol) of morpholine, 0.231 g (2.4 mmol) of sodium t-butoxide, 4.5 mg (1 mol % based on the amine) of palladium acetate, and 15.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 14 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.304 g (81%) of N-(4-cyanophenyl)morpholine as light-yellow crystals. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.466 g (2.00 mmol) of 4-bromobiphenyl and 4 mL of toluene under a nitrogen atmosphere. The bromobiphenyl was dissolved in the solvent. To this solution were added 0.399 g (2.2 mmol) of benzophenonimine, 0.231 g (2.4 mmol) of sodium t-butoxide, 13.5 mg (3 mol % based on the amine) of palladium acetate, and 46.9 mg (6 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 16 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.409 g (61%) of N-(diphenylmethylene)-4-aminobiphenyl as a yellow oily substance. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.330 g (1.93 mmol) of p-tolyl bromide and 4 mL of toluene under a nitrogen atmosphere. The bromide was dissolved in the solvent. To this solution were added 0.266 g (2.16 mmol) of p-anisidine, 0.226 g (2.35 mmol) of sodium t-butoxide, 8.5 mg (1 mol % based on the amine) of tris(dibenzylidene)dipalladium, and 32.3 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 5 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.366 g (89%) of N-p-methoxyphenyl-N-p-tolylamine. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 0.214 g (2.00 mmol) of p-toluidine and 4 mL of dioxane under a nitrogen atmosphere. The amine was dissolved in the solvent. To this solution were added 0.515 g (2.2 mol) of p-iodoanisole, 0.231 g (2.4 mmol) of sodium t-butoxide, 4.5 mg (1 mol % based on the amine) of palladium acetate, and 15.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 8 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.351 g (82%) of N-p-methoxyphenyl-N-p-tolylamine as yellow crystals. The results obtained are shown in Table 20. The resultant reaction mixture cooled this mixture was extracted with toluene The extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was purified by column chromatography

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reactor were introduced 8.50 g (31.1 mmol) of the 2-bromo-1,1-diphenylpropene obtained in Example 1 (2) and 85 ml of THF under a nitrogen atmosphere. The contents were cooled to −70° C. Thereto was gradually added dropwise 21.4 mL (34.2 mmol; 1.6 M hexane solution) of butyllithium. The resultant mixture was stirred for 30 minutes. Thereafter, 8.25 mL (37.3 mmol) of chlorodicyclohexylphosphine was added, and this mixture was stirred for 75 minutes, subsequently heated to room temperature, and then further stirred for 15.5 hours. Water was added to the reaction mixture. The organic layer was extracted with ethyl acetate, and the extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol to obtain 8.80 g (72%) of the target compound as white crystals. subsequently heated to room temperature further stirred for 15.5 hours The organic layer was extracted with ethyl acetate the extract was dried with anhydrous magnesium sulfate Thereafter, the solvent was removed under reduced pressure The concentrate was recrystallized from ethanol