- Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation
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The selective functionalization of C-H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably general protocol which results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) and uses standard borylation ligands. Our strategy hinges upon the facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation. We hypothesize that the bulk of this cation disfavors meta-C-H borylation, thereby promoting the challenging para-selective reaction.
- Mihai, Madalina T.,Williams, Benjamin D.,Phipps, Robert J.
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supporting information
p. 15477 - 15482
(2019/10/11)
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- 1,3,4-OXADIAZOLE SULFONAMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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The present invention relates to novel compounds represented by the formula I having histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. (I) The novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase (HDAC) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases.
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Paragraph 1137; 1139; 1139
(2017/02/24)
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- Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-N-Ms-arylamines with Benzyl Halides/Sulfonates
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An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram-scale preparation.
- Yang, Si-Yi,Han, Wen-Yong,Zhang, Ding-Lei,Zhou, Xiao-Jian,Bai, Mei,Cui, Bao-Dong,Wan, Nan-Wei,Yuan, Wei-Cheng,Chen, Yong-Zheng
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p. 996 - 1003
(2017/02/15)
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- Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
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An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.
- Xiong, Xiaodong,Yeung, Ying-Yeung
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supporting information
p. 16101 - 16105
(2016/12/26)
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- Low catalyst loadings for ligand-free copper(I)-oxide-catalyzed N-arylation of methanesulfonamide in water
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A simple and practical protocol for the cross-coupling of methanesulfonamide and aryl iodides under ligand-free copper(I)-oxide-catalyzed conditions in water is reported. The method allows the preparation of a wide variety of synthetically useful N-arylated methanesulfonamides in good to excellent yields (up to 90 %) under the optimized conditions. A convenient and efficient ligand-free method using a copper(I) oxide catalyst at 130 °C in water was developed for the N-arylation of methanesulfonamide with aryl iodides. A variety of functionalized aliphatic and cyclic sulfonamides were coupled with different substituted aryl halides to give the corresponding N-arylated products in good to excellent yields under the optimized conditions. Copyright
- Tan, Bryan Yong-Hao,Teo, Yong-Chua,Seow, Ai-Hua
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p. 1541 - 1546
(2014/03/21)
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- Low Catalyst Loadings for Ligand-Free Copper(I)-Oxide-Catalyzed N-Arylation of Methanesulfonamide in Water
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A simple and practical protocol for the cross-coupling of methanesulfonamide and aryl iodides under ligand-free copper(I)-oxide-catalyzed conditions in water is reported. The method allows the preparation of a wide variety of synthetically useful N-arylated methanesulfonamides in good to excellent yields (up to 90 %) under the optimized conditions.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua,Seow, Ai-Hua
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p. 1541 - 1546
(2015/10/05)
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- Discovery and SAR of a novel series of non-MPEP site mGlu5 PAMs based on an aryl glycine sulfonamide scaffold
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Herein we report the discovery and SAR of a novel series of non-MPEP site metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulators (PAMs) based on an aryl glycine sulfonamide scaffold. This series represents a rare non-MPEP site
- Rodriguez, Alice L.,Zhou, Ya,Williams, Richard,David Weaver,Vinson, Paige N.,Dawson, Eric S.,Steckler, Thomas,Lavreysen, Hilde,MacKie, Claire,Bartolomé, José M.,MacDonald, Gregor J.,Scott Daniels,Niswender, Colleen M.,Jones, Carrie K.,Jeffrey Conn,Lindsley, Craig W.,Stauffer, Shaun R.
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p. 7388 - 7392
(2013/02/23)
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- Electron transfer activity of a cobalt crown carbene complex
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The novel cobalt(II) crown carbene complex 12(II) has been prepared and characterised by X-ray crystallography. This complex is reduced in a one-electron process to a cobalt(I) complex that acts as a powerful single electron donor, reducing aryl halides,
- Park, Stuart R.,Findlay, Neil J.,Garnier, Jean,Zhou, Shengze,Spicer, Mark D.,Murphy, John A.
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supporting information; experimental part
p. 10756 - 10761
(2010/03/01)
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- Convenient synthesis of primary sulfonamides
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An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.
- Greenfield, Alexander,Grosanu, Cristina
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body text
p. 6300 - 6303
(2009/04/06)
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- Base-free monosulfonylation of amines using tosyl or mesyl chloride in water
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A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.
- Kamal, Ahmed,Reddy, J. Surendranadha,Bharathi, E. Vijaya,Dastagiri
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p. 348 - 353
(2008/09/17)
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- A convenient reductive deamination (hydrodeamination) of aromatic amines
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Reductive deamination (hydrodeamination) of aromatic amines can be conveniently carried out by amination of the corresponding arylamine methanesulfonamides using chloroamine under alkaline conditions. The intermediate aryl methanesulfonylhydrazines directly eliminate methanesulfinic acid, affording diazenes which extrude nitrogen affording the desired deaminated products. Both sulfonamide formation and reduction reactions occur in high yield and are compatible with a variety of functional groups.
- Wang,Guziec Jr.
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p. 8293 - 8296
(2007/10/03)
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