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With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 25h;Inert atmosphere; Schlenk technique;
General procedure: An oven-dried Schlenk tube was charged with a magneticstir bar, binucleophile 2-mercaptobenzimidazole 2 (1.0 mmol, 1.0 equiv), CuI(0.1 mmol, 10 mol %), phen (0.2 mmol, 20 mol %), and K2CO3 (2.0 mmol, 2equiv). The tube was capped and then evacuated and backfilled with nitrogen(3 times). Under a positive pressure of nitrogen, a solution of o-dihaloarene 1(1.05 mmol, 1.05 equiv) in DMF (3 mL) was added via syringe. The tube wassealed and allowed to stir at 120 C (monitored by TLC). After being cooled toroom temperature, EtOAc (40 mL) was added and the mixture was washedwith brine (20 mL 3). The organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silicagel using petrol/EtOAc (10:1?3:1, v:v) as eluent to give product 3.
9-[4-cyano-2-(9-phenanthryl)phenyl]phenanthrene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
31%
With potassium carbonate; XPhos; In tetrahydrofuran; water; at 75℃; for 15h;Inert atmosphere; Schlenk technique;
In a nitrogen stream, in a 50 mL Schlenk tube,3.52 g (11.43 mmol) of <strong>[1000577-94-5]3-bromo-4-iodobenzonitrile</strong>, 6.35 g (28.58 mmol) of 9-phenanthreneboronic acid,51 mg (0.23 mmol),218 mg (0.46 mmol) of 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (Xphos), 15 mL of tetrahydrofuran,And 15 mL of 2 M potassium carbonate aqueous solution were added, and the mixture was stirred at 75 C. for 15 hours. After cooling to room temperature, methanol 100 mL was added and stirred, and the precipitated solid was collected by filtration and washed with pure water and methanol.By recrystallizing (chloroform / methanol) the residue,1.62 g (3.56 mmol) of a colorless powder of 9- [4-cyano-2- (9-phenanthryl) -phenyl] - phenanthrene was isolated (yield 31%, HPLC purity 98.4%).
2'-oxo-2,3-diphenyl-2'H-spiro[indene-1,1'-naphthalene]-6-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67%
With palladium diacetate In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;
6 Example 6
Under argon, 0.02 mmol palladium acetate, 0.3 mmol reactant 1f, 0.3 mmol reactant 2a,0.3 mmol reactant 3a, 0.4 mmol potassium phosphate, 2.0 mL 1,4-dioxane, then heated to 130 in an oil bath, and reacted for 16 hours. After the reaction, the reaction solution was directly spin-dried, and the target product was separated by column chromatography2'-Oxo-2,3-diphenyl-2'H-spiro[indene-1,1'-naphthalene]-6-carbonitrile (4f). Product data characterization: white solid (56.5 mg, yield: 67%).
67%
With potassium phosphate; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 72℃; for 3h; Inert atmosphere;
5.1.1.1
The 2-bromo-4 cyano iodobenzene (30.7g, 100mmol),4-chlorophenylboronic acid (15.6g, 100mmol),Add under nitrogen protectionTetratriphenylphosphine palladium 1.15g,Potassium carbonate 27.6g,Add 200mL of toluene,150mL of ethanol,100mL of water,Heated to 72°C,Stir for 3h;And then cooled to room temperature,Add the reaction solution after washing with waterMagnesium sulfate drying,After filtration, the filtrate was decompressed to remove the solvent;Use toluene to recrystallize the crude product(1g crude product: 10mL toluene) purification,Obtained 16.35g white solid product E-1 (56mmol, yield 56%)
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