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With indium(III) triflate; triethylsilane In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere; chemoselective reaction;
25 4.2. General procedure for indium-catalyzed reductive synthesis of azobenzene compounds
General procedure: To a 5 mL screw vial under N2 containing a freshly distilled DMF (0.6 mL) were successively added aromatic nitro compound (0.60 mmol), In(OTf)3 (0.030 mmol, 17 mg), and Et3SiH (1.80 mmol, 287 μL). The resulting mixture was stirred at 60 °C (bath temperature), and monitored by TLC analysis. After completion of the reaction, the resultant mixture was further stirred under either an ambient or an O2 atmosphere during the corresponding reaction time. The reaction was quenched with H2O (6 mL). The aqueous layer was extracted with AcOEt (6 mL×3), the combined organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by recrystallization from the solvent (hexane/chloroform) or silica gel column chromatography (hexane/AcOEt) to afford the corresponding azobenzene derivatives.
95%
With isopropyl alcohol for 20h; UV-irradiation; Green chemistry;
94%
With sodium ethanolate; acetophenone In ethanol at 160℃; for 5h;
85%
With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 4h; Reflux;
75%
With ammonium chloride; dimethyl sulfoxide at 20℃; Electrochemical reaction; Green chemistry;
69%
With ammonia; lithium perchlorate In methanol at 20℃; for 6h; Electrolysis; chemoselective reaction;
60%
With bismuth; potassium hydroxide In methanol for 0.133333h; Microwave irradiation;
With lithium aluminium tetrahydride; diethyl ether; benzene
With potassium hydroxide; pyrographite; hydrazine hydrate; ruthenium
With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 115℃; for 16h; Inert atmosphere;
1: 22%
2: 37%
With 1,10-Phenanthroline; oxygen; sodium hydrogencarbonate; copper(II) sulfate In N,N-dimethyl-formamide; toluene at 150℃; for 24h; Molecular sieve; Schlenk technique;
Multi-step reaction with 2 steps
1: potassium <i>tert</i>-butylate / ethanol / 20 °C
2: tetraethoxy orthosilicate; oxygen; copper diacetate; silver trifluoromethanesulfonate / N,N-dimethyl-formamide / 18 h / 145 °C
With 1,10-Phenanthroline; di-tert-butyl peroxide; oxygen; potassium carbonate; copper(I) bromide In toluene at 140℃; for 24.25h; Molecular sieve; Schlenk technique; Sealed tube; regioselective reaction;
Multi-step reaction with 3 steps
1: acetonitrile / 2 h / 20 °C / Darkness
2: acetonitrile / Darkness
3: d<SUB>7</SUB>-N,N-dimethylformamide / 24 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness
With nitric acid In acetic anhydride at -5℃; for 24h; regioselective reaction;
General Procedure of Nitration.
All reactions were carried out in a 50 mL one-necked round bottomed flask equipped with a water condenser and a magnetic stirrer. In a typical experiment, a mixture of zeolite HBEA-500 (0.30 g) which was calcined at 550 °C for 2 h in air prior to use, biphenyl (0.61 g, 4 mmol), nitric acid (95%, 0.35 mL, 8 mmol) was stirred in acetic anhydride (5.0 mL) at -5 °C for 24 h. When the reaction was over, 10 mL of dichloromethane was added, then the zeolites was removed by filtration and the filtrate was washed with water (3 × 10 mL) and 5% aqueous solution of NaHCO3 (10 mL) and water (3× 10 mL). The organic phase separated was dried with anhydrous sodium sulfate, and filtrated to give a straw yellow liquid. The isomer distribution and yields of products were estimated from the peak areas based on the internal standard technique using gas chromatography. The straw yellow products with further purification by column chromatography, and were identified by comparison of their analytical data with those of authentic samples.
With nitric acid In dichloromethane for 20h; Reflux;
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