- Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
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A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.
- Maity, Saurabh,Das, Debapratim,Sarkar, Souradip,Samanta, Rajarshi
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supporting information
p. 5167 - 5171
(2018/09/13)
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- Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides
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Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.
- Lee, Yong Ho,Morandi, Bill
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p. 1016 - 1022
(2018/09/06)
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- One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
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A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.
- Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.
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supporting information
p. 2518 - 2521
(2017/05/24)
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- Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
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The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.
- Li, Lu,Liu, Wenbo,Zeng, Huiying,Mu, Xiaoyue,Cosa, Gonzalo,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 8328 - 8331
(2015/07/15)
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- Iron(II)-catalyzed direct cyanation of arenes with aryl(cyano)iodonium triflates
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A direct oxidative cyanation of arenes under FeII catalysis with 3,5-di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds. Copyright
- Shu, Zhibin,Ji, Wenzhi,Wang, Xi,Zhou, Yujing,Zhang, Yan,Wang, Jianbo
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p. 2186 - 2189
(2014/03/21)
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- Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation
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A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.
- Partridge, Benjamin M.,Hartwig, John F.
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p. 140 - 143
(2013/03/28)
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- Elemental fluorine. Part 4. Use of elemental fluorine for the halogenation of aromatics
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New methodolgy for direct iodination of benzenoid compounds has been developed; the aromatic substrate is simply mixed with iodine and sulfuric acid, suspended in an inert medium, such as 1,1,2-trichlorotrifluoroethane (CF2ClCFCl2) or perfluorocarbon, and elemental fluorine is passed through the system at room temperature. High conversions to iodoaromatic products occur, even with some deactivated systems, e.g. nitrobenzene. A very powerful brominating system is produced using the analagous methodology.
- Chambers, Richard D.,Skinner, Christopher J.,Atherton, Malcolm J.,Moilliet, John S.
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p. 1659 - 1664
(2007/10/03)
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- Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines
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There is provided an insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a tetrahydroquinazoline compound of the formula STR1 wherein R, R1, R2, R3, R5, R6, R7, R8, and R9 are as defined herein, and methods of using the same. Certain novel substituted-phenyl tetrahydroquinazoline compounds per se are also identified.
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- Syntheses and lipophilicities of tetraarylborate ions substituted with many trifluoromethyl groups
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Syntheses were investigated using various tetraarylborate ions with a large number of trifluoromethyl groups: tetrakisborate; tetrakisborate; tetrakisborate; and tetrakisborate ions.The preparation of Grignard reagents and the subsequent reaction with boron trifluoride etherate are importantsteps for a higher yield and easier isolation of the product.Sodium- and tetramethylammonium salts of these borate ions are soluble in halocarbon solvents such as dichloromethane, chloroform and 1,2-dibromotetrafluoroethane.
- Fujiki, Kanji,Kashiwagi, Mitsuyoshi,Miyamoto, Hideyuki,Sonoda, Akinari,Ichikawa, Junji,et al.
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p. 307 - 321
(2007/10/02)
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- Rodenticidal 1-(3,5-bistrifluoromethylphenyl)-3-(4-t-butylpiperidino)prop-1-yne
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The hitherto unknown phenylpropargylamine derivative 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne, and acid addition salts thereof, have been found to be useful for killing warm-blooded vermin, especially rodents. Processes for the preparation of the new phenylpropargylamine derivative are described and so are suitable rodenticidal compositions.
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