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4,5-dimethoxy-2-(2-methallyl)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1: 71%
2: 10%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water Reflux; Inert atmosphere;
General procedure to prepare ene-substrate from different 2-formylphenylboronic acids
General procedure: To a solution of 8 methallyl bromide (2equiv) in 94 THF (0.2M) in a two neck round bottom flask were added 9 PdCl2(PPh3)2 (2.5mol%) and aqNa2CO3 (1M, 2equiv). This solution was degassed with inert gas. To this, a degassed solution of 95 2-formylphenylboronic acid (0.25equiv) was added and the resulting mixture was heated at reflux. After 1h, the reaction mixture was cooled to rt, and another 0.25equiv degassed solution of the 96 boronic acid was added. After 6-7h, the reaction mixture was cooled and quenched with water (3mL/mmol) and extracted with DCM (3×10mL/mmol). The combined organic layer was washed with brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel.
2-(inden-2-yl)-4,5-dimethoxybenzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
With palladium diacetate; tris-(o-tolyl)phosphine; barium(II) hydroxide In 1,2-dimethoxyethane; water at 50℃; for 2h;
2-(Inden-2-yl)benzaldehyde (16a)
General procedure: A mixture of triflate 10 (140 mg, 0.52 mmol), phenylboronic acid 15a (117 mg, 0.78 mmol), Ba(OH)2 (265 mg, 0.78 mmol), P(o-tolyl)3 (30 mg, 0.1 mmol), and Pd(OAc)2 (12 mg, 0.052 mmol) in DME/H2O (4.3/0.7 mL) was stirred at 50 °C for 2 h. The reaction mixture was quenched with water, and then the mixture was extracted with EtOAc. The EtOAc layer was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane (1:9, v/v) as an eluent to give the arylindene 16a (74 mg, 65%) as orange oil.
6-phenyl-12-(m-tolyl)-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine[ No CAS ]
4,5-dimethoxy-3'-methyl-[1,1'-biphenyl]-2-carbaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With 1,1'-bis-(diphenylphosphino)ferrocene; caesium carbonate; Selectfluor; palladium dichloride In tetrahydrofuran at 80℃; for 8h; Schlenk technique; Inert atmosphere;
2-methyl-N-(3-phenylprop-2-yn-1-yl)-N-tosylacrylamide[ No CAS ]
5,6-dimethoxy-4',4'-dimethyl-2-phenyl-1'-tosylspiro[indene-1,3'-pyrrolidine]-3,5'(2H)-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With (S,S)-[2-(4'-isopropyloxazolin-2'-yl)ferrocenyl]diphenylphosphine; nickel(II) acetate tetrahydrate In 1-methyl-pyrrolidin-2-one at 100℃; for 36h; Sealed tube; Inert atmosphere; enantioselective reaction;
Multi-step reaction with 2 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 8 h / 80 °C / Inert atmosphere
2.1: sodium periodate / tetrahydrofuran; water / 0.33 h / 20 °C
2.2: 2 h / 20 °C
Multi-step reaction with 2 steps
1.1: montmorillonite K-10 / dichloromethane / 0.5 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C
2.2: 1 h / -78 °C
2.3: -78 - 5 °C
Stage #1: 4,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde With sodium periodate In tetrahydrofuran; water at 20℃; for 0.333333h;
Stage #2: With hydrogenchloride In water at 20℃; for 2h;
Stage #1: 2-bromo-4,5-dimethoxybenzaldehyde dimethyl acetal With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran; cyclohexane at -78℃; for 1h;
Stage #3: With hydrogenchloride In tetrahydrofuran; cyclohexane; water at -78 - 5℃;
3-(1-(tert-butyl)-1H-tetrazol-5-yl)-5,6-dimethoxybenzo[c][1,2]oxaborol-1(3H)-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
Stage #1: (2-formyl-4,5-dimethoxyphenyl)boronic acid With trimethylsilylazide In neat (no solvent) for 0.0833333h;
Stage #2: tert-butylisonitrile In neat (no solvent) at 20℃; for 3h;
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