| 78% |
With potassium carbonate; In water; at 60℃; for 16h;Green chemistry; |
General procedure: A mixture of Fe3O4(at)SiO2-NHC-Pd(II) (0.006 g, 0.37 mol%), arylboronic acid (1.1 mmol), aryl halide (1.0 mmol), and K2CO3(2 mmol) in H2O (3 mL)was stirred at 60 C for the appropriate timeas indicated in Table 3. The completion of the reaction was monitoredby TLC. After completion of the reaction, the catalyst wasremoved by an external magnetic field and was then washed withH2O (5 mL) and ethyl acetate (10 mL). The organic layer was separated,dried over anhydrous Na2SO4, and filtered. Then, the solventwas evaporated under reduced pressure. The pure product wasobtained via silica gel column chromatography with an eluent of nhexaneand ethylacetate. |
|
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 60℃; for 24h;Inert atmosphere; Sealed vessel; |
Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison. |
| 94%Chromat. |
With [Pd2(μ-1,1′-bis(diphenylphosphino)ferrocene)(4-methoxy-N′-(mesitylidene)benzohydrazide)2]; tetrabutylammomium bromide; potassium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 12h; |
General procedure: An oven-dried round bottom flask (10 ml) was charged with 0.1ml dimethylformamide solution of complex IV (0.1 mol % for aryl bromides and 0.2 mol % for aryl chlorides), aryl boronic acid (1.2 mmol), aryl halide (1.0 mmol), K2CO3 (1.5 mmol), TBAB (1.0 mmol) and 2 ml water. The reaction mixture was then heated (to 70 C for aryl bromides and 90 C for aryl chlorides) with stirring under aerobic conditions for the required time. At the end of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×5 ml). The combined extract was washed with water (2×10 ml), dried over anhydrous sodium sulfate and then subjected to GC-MS analysis for identification and yield determination (from the areas under the peaks) of the products. In the case of reactions with 2-naphthylboronic acid, the combined extract was evaporated to dryness under reduced pressure and the residue was purified by column chromatography (silica gel, ethyl acetate/n-hexane) to afford the coupling products. The products were identified by 1H and 13C NMR and HR-MS analysis. |
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