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1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With ammonium chloride; at 110℃;Inert atmosphere;
General procedure: In a flask, the imine (1.3 g, 4.45 mmol) was suspended in ethyl alcohol (65 ml), then cooled to 0 C and sodium borohydride (3.36 g, 89 mmol) was added slowly, after stirring for 30 min, the mixture was heated to reflux until the color of the solution turn into colorless. Cool to room temperature, then aqueous saturated sodium chloride (12 ml) was added to stir for 30 min, after that, 50 ml water and 40 ml chloroform was added, then organic phase was separated, washed with small amount of water, dried under anhydrous sodium sulfate, and then volatiles were removed under vacuum, yielding light yellow oil. The oil was purged to next step. In the same flask, ammonium chlorite (261.9 mg, 4.9 mmol) and triethyl orthoformate (4 ml) was added, the mixture was stirred under N2 at 110 C overnight, then ethyl ether was added to separated yellow solid, filtered and then recrystallized by dichloromethane and ethyl ether, affording 1.3 g yellow SIMes·HCl in 85% yield.
With potassium carbonate In tetrahydrofuran at 80℃; for 24h; Glovebox;
Synthesis of compound 6
An oven-dried 4 mL of vial with stir bar was charged with 4 (0.021 g, 0.05 mmol) and K2CO3 (0.007 g, 0.05 mmol) in the glove box. The vial was capped and moved out from the glove box, then CS2 (0.5 mmol, 30 μL) and 2 mL of THF were injected into the vial by syringe. The reaction was stirred at 80 °C for 24 h until a red solid was formed and precipitated. The resulting mixture was filtered through a plug of Celite, and washed by DCM. The volatiles were removed by rotavapor, and the product was isolated by chromatography with DCM as eluent with 95 % yield.
86%
With caesium carbonate In acetonitrile at 20℃; for 4h;
34%
Stage #1: 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: carbon disulfide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #1: 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; Alkaline conditions; Flow reactor;
Stage #2: carbon disulfide In tetrahydrofuran at 20℃; Flow reactor;
1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride[ No CAS ]
[ 578743-87-0 ]
Yield
Reaction Conditions
Operation in experiment
81%
With sodium t-butanolate; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; Schlenk technique;
An oven-dried Schlenk flask containing 1,3-bis(2,6-di-iso-propylphenyl)imidazolium chloride (849.0 mg, 2.00 mmol), CuCl (198.0 mg, 2.00 mmol), NaOtBu (192.0 mg, 2.00 mmol) was evacuated and refilled with argon three times. THF (10 mL) were added to this Schlenk flask. The resulting suspension was stirred at room temperature for 4 h. Then, it was filtered through Celite in glovebox.The title compound was obtained as a white powder (788.6 mg, 81% yield).
9 Example 9 Synthesis of complex Cu-8 (C27H38ClCuN2)
In a 50mL flask, add ligand 427mg (1.0mmol),Copper phenylacetylene 182mg (1.1mmol), acetonitrile 15mL, in an oil bath at 40 ~ 50 ,The reaction was stirred for 20 hours, and the reaction mixture was cooled to room temperature and filtered.The filtrate was distilled under reduced pressure to remove the solvent to obtain 446 mg of colorless crystals with a yield of 91%.
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