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With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 15 - 25℃; for 3h;
General procedure: A 5 mL round bottom flask was charged with 0.1 g of indole and 2.0 mL of DMSO. To the resultant solution was added NIS (1.2 equiv)/IBX (3.0 equiv), and the reaction mixture was stirred at 20 ± 5 C.Progress of the reaction was monitored by TLC (thin layer chromatography) analysis. After completion ofthe reaction, the reaction mixture was diluted with 20 mL of ethyl acetate, and the organic phase was washed with saturated solution of Na2S2O3 followed by brine, and then dried over anhyd. Na2SO4. Subsequently, the extract was stripped off the solvent under reduced pressure, and the product was isolated by silica gel column chromatography.
71%
With tert.-butylhydroperoxide; copper diacetate; In water; acetonitrile; at 50℃; for 12h;Catalytic behavior;
General procedure: Cu(OAc)2 (0.025 mmol), indoles (0.5 mmol), TBHP (1 mL, 70 % solution in water) and CH3CN (3.0 mL) were added to glass tube via syringe. The reaction mixture was stirred at 50C for 12 h. It was then quenched (consumption of residual TBHP) with saturated Na2SO3 solution and extracted with EtOAc. The organic layer was combined and dried with Na2SO4. Removal of solvent followed by flash column chromatographic purification (Ethyl acetate/Petroleum ether=5/1) afforded products.
69%
With tert.-butylhydroperoxide; palladium diacetate; In water; acetonitrile; at 80℃; for 1h;
General procedure: Pd(OAc)2 (0.05 mmol), indole derivative 1 (0.5 mmol), TBHP (1 mL, 70 % solutionin water) and CH3CN (3.0 mL) were added to a vial. The reaction mixture was stirredunder 80 C for 1 h. After that time, the reaction mixture was quenched with saturatedNa2SO3 solution (consumption of residual TBHP) and extracted with EtOAc. Theorganic layer was separated and dried with Na2SO4. Removal of solvent followed byflash column chromatographic purification (Ethyl acetate/Petroleum ether = 5/1)afforded products.
With tert.-butylhydroperoxide; iodine; In dimethyl sulfoxide; at 90℃; for 24h;
General procedure: N-methyl indole (0.5 mmol), DMSO (5 ml) were added into reaction tube and stirred at 90 C. Then the I2 (0.6 mmol) and TBHP (2.5 mmol) were added into the reaction tube. After 24 h the o-benzenediamine (0.34 mmol) was added into the mixture. The reaction was stopped until the o-benzenediamine was completely consumed as monitored by TLC analysis. After the completion of reaction, 5% Na2S2O3 solution (30 mL) was added to the mixture. The mixture was extracted with EtOAc (3 * 20 ml) and the organic layer was dried by Na2SO4. Then the crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate/dichloromethane 3/1/1).
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