Method for synthesizing polysubstituted allene under catalysis of nickel
A multi-substituted, nickel-catalyzed technology, used in chemical instruments and methods, preparation of organic compounds, separation/purification of carbonyl compounds, etc., can solve the problems of free radical limitation, poor atom economy, etc. Simple, responsive and economical
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Embodiment 1
[0030] S1: Add ethylene glycol dimethyl ether nickel bromide (6.2mg, 0.02mmol, 0.1equiv), 2-benzoyl-1,3-enyne (57.6mg, 0.2mmol, 1.0equiv), zinc powder (39mg , 0.6mmol, 3.0 equiv), 2,2'-bipyridine (4.7mg, 0.03mmol, 0.15equiv), put magnets into the reaction tube, after weighing, vacuumize the reaction tube-release nitrogen cycle 3 times , then added dry N,N-dimethylacetamide (2 mL) and bromide (108.4 mg, 0.4 mmol) to the reaction tube under nitrogen, and sealed the rubber stopper with parafilm.
[0031] S2: place the reaction tube treated by S1 at room temperature and stir for 24 hours, then stop the reaction;
[0032] S3: Add 6 mL of saturated ammonium chloride solution to the reaction solution treated in step S2 and stir for 30 min. The aqueous phase after layering is extracted with ethyl acetate (4×10 mL), and the combined organic phases are washed with 5 mL of saturated brine. MgSO for organic phase 4 After drying for 15min, filter, and the filtrate is rotary evaporated to...
Embodiment 2
[0039] S1: Put magnets into the reaction tube, add ethylene glycol dimethyl ether nickel bromide (6.2mg, 0.02mmol, 0.1equiv), 2-benzoyl-1,3-enyne (63.7mg, 0.2mmol , 1.0equiv), zinc powder (39mg, 0.6mmol, 3.0equiv), 2,2'-bipyridine (4.7mg, 0.03mmol, 0.15equiv). After weighing, the reaction tube was vacuum-released nitrogen cycle 3 times, then dry N,N-dimethylacetamide (2 mL) and tert-butyl bromide (54.8 mg, 0.4 mmol ), seal the rubber stopper tightly with a parafilm;
[0040] S2: place the reaction tube treated by S1 at room temperature and stir for 24 hours, then stop the reaction;
[0041] S3: Add 6 mL of saturated ammonium chloride solution to the reaction solution treated in step S2 and stir for 30 min, extract the layered aqueous phase with ethyl acetate (4×10 mL), wash the organic phase once with 5 mL of saturated saline, and combine MgSO for organic phase 4 Dry for 15 minutes, filter, and remove the solvent by rotary evaporation of the filtrate;
[0042] S4: Use a mi...
Embodiment 3
[0048] S1: Put magnets into the reaction tube, add ethylene glycol dimethyl ether nickel bromide (6.2mg, 0.02mmol, 0.1equiv), 2-benzoyl-1,3-enyne (63.7mg, 0.2mmol , 1.0equiv), zinc powder (39mg, 0.6mmol, 3.0equiv), 2,2'-bipyridine (4.7mg, 0.03mmol, 0.15equiv). After weighing, the reaction tube was vacuum-released nitrogen cycle 3 times, and then dry N,N-dimethylacetamide (2 mL) and homobenzyl bromide (85.2 mg, 0.4 mmol) were added to the reaction tube under nitrogen , seal the rubber stopper tightly with parafilm. ;
[0049] S2: After the reaction tube was placed at room temperature and stirred for 24 hours, the reaction was stopped;
[0050] S3: Add 6mL of saturated ammonium chloride solution to the reaction solution and stir for 30min, the aqueous phase after layering is extracted with ethyl acetate (4×10mL), and the organic phases are combined with MgSO 4 Dry for 15 minutes, filter, and remove the solvent by rotary evaporation of the filtrate;
[0051] S4: Then use a mi...
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