612-55-5Relevant articles and documents
The Oxyiodination of Aromatic Compounds over Zeolite KX: The Case of Naphthalene
Tustin, Gerald C.,Rule, Mark
, p. 186 - 198 (1994)
Aromatic compounds, iodine, and oxygen react in the vapor phase over basic faujasite zeolites at 225-350 deg C to produce iodoaromatic compounds and water.When the aromatic compond is naphthalene and the reaction is conducted in the region of 250 deg C over KX zeolite, a shape-selective catalytic oxyiodination occurs, resulting in predominant iodination at the 2-position of naphthalene.Typical product mixtures contain approximately 10percent 1-iodonaphthalene, 65percent 2-iodonaphthalene, 19percent 2,6-diiodonaphthalene, 5percent other diiodonaphthalene isomers, and 1percent mixed triiodonaphthalene isomers at approximately 20percent naphthalene conversion and 80-99percent iodine conversion.Excessive conversion and excessive residence time reduce the selectivity to kinetic product, 2,6-diiodonaphthalene, but do not alter the selectivity for iodination in the 2-position.Selectivity for iodination in the 2-position is decreased by substituting sodium for potassium in the zeolite, by alterning the faujasite zeolite Si/Al ratio significantly above or below 1.25 and by increasing the amount of iodine in the reactant feed.
Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO
Zhu, Yamin,Li, Linyi,Shen, Zengming
supporting information, p. 13246 - 13252 (2015/09/15)
The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide). The broad substrate scope includes a variety of electron-rich and electron-poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN- moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper. The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system. Electron-rich and electron-poor arylboronic acids react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent. Moreover, TEMPO, a cheap oxidant, enables the reaction to be catalytic in copper (see scheme; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide).
Comparative study of the reactivity of iodinating agents in solution and solid phase
Krasnokutskaya,Lesina,Gorlushko,Filimonov
, p. 855 - 859 (2007/10/03)
The results of reactions of a series of aromatic substrates with iodine, iodine(I) chloride, and N-iodosuccinimide in solution and solid phase were compared for the first time. In all cases, the general relations holding in the iodination process were similar. Iodine(I) chloride was found to chlorinate anthracene. A high efficiency of solid-phase iodination of β-diketones was demonstrated using dibenzoylmethane as an example.
