2010
DOI: 10.1590/s0103-50532010000100002
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A mild and simple iodination of phenols with trichloroisocyanuric acid/ I2 /Wet SiO2 system

Abstract: Iodo molecular na presença de ácido tricloroisocianúrico e solução aquosa de SiO 2 foi utilizado com eficiência na iodinação de fenóis em condições reacionais brandas.Molecular iodine in the presence of trichloroisocyanuric acid and wet SiO 2 has been utilized efficiently for iodination of phenols under mild reaction conditions.

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Cited by 7 publications
(3 citation statements)
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“…Bromide 4a is commercially available. We investigated several ways to prepare the corresponding iodide 4b from 1,4-dimethoxybenzene, among them iodine in the presence of trichlorocyanuric acid and silica gel [9], I 2 /periodic acid [10], I 2 /silfen [11], N -iodosuccinimide [12], and potassium iodide/potassium iodate [13]. In our hands the best yields of 4b were obtained using iodine in the presence of silfen [11].…”
Section: Resultsmentioning
confidence: 99%
“…Bromide 4a is commercially available. We investigated several ways to prepare the corresponding iodide 4b from 1,4-dimethoxybenzene, among them iodine in the presence of trichlorocyanuric acid and silica gel [9], I 2 /periodic acid [10], I 2 /silfen [11], N -iodosuccinimide [12], and potassium iodide/potassium iodate [13]. In our hands the best yields of 4b were obtained using iodine in the presence of silfen [11].…”
Section: Resultsmentioning
confidence: 99%
“…Inactive I-P3CA was synthesized according to the method of Akhlaghinia and Rahmanib, with slight modifications [24]. P3CA (20.0 mg, 0.05 mmol), iodogen (21.2 mg, 0.05 mmol), SiO 2 (25.0 mg, 0.42 mmol), and iodine (12.4 mg, 0.05 mmol) were dissolved in 5.0 mL methane dichloride.…”
Section: Labeling Proceduresmentioning
confidence: 99%
“…They are also important and the most reactive intermediates for various cross-coupling reactions and especially useful for formation of carbon-carbon and carbon-heteroatom bonds [4]. Recently the reagents reported for iodination of arenes include, iodine-nitrogen dioxide [5], iodine F-TEDA-[1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2,2,2] octane-bis-(tetrafluoroborate)] [6], bis-N-iodosuccinimide [7], trichloroisocyanuric acid-I2-Wet SiO2 [8], mercury(II)-oxide-iodine [9], iodine-monochloride [10], bis(pyridine)iodonium(I), tetrafluoroborate CF3SO3H [11], NIS-CF3SO3H [12], iodine silver sulfate [13], iodine-mercury salts [14] and NaOCl-NaI [15]. However, most of these methods suffer from major drawbacks such as use of harsh conditions, toxic heavy-metal catalysts, non-slectivity and longer reaction times.…”
Section: Introductionmentioning
confidence: 99%