4703-17-7Relevant academic research and scientific papers
Sterically Congested 2,6-Disubstituted Anilines from Direct C?N Bond Formation at an Iodine(III) Center
Lucchetti, Nicola,Scalone, Michelangelo,Fantasia, Serena,Mu?iz, Kilian
supporting information, p. 13335 - 13339 (2016/10/30)
2,6-Disubstituted anilines are readily prepared from the direct reaction between amides and diaryliodonium salts. As demonstrated for 24 different examples, the reaction is of unusually broad scope with respect to the sterically congested arene and the nitrogen source, occurs without the requirement for any additional promoter, and proceeds through a direct reductive elimination at the iodine(III) center. The efficiency of the coupling procedure is further demonstrated within the short synthesis of a chemerin binding inhibitor.
Transition-metal-free direct amination of simple arenes with sulfonyl azides
Wang, Lianggui,Borah, Arun Jyoti,Yan, Guobing
supporting information, p. 1353 - 1355 (2015/03/04)
A metal-free green protocol has been developed for amination of simple arenes using arylsulfonyl azides via a nitrene transfer process under solvent free conditions at 130 °C releasing N2 gas as the sole by-product.
Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
, p. 3504 - 3511 (2015/04/14)
One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
Palladium-Catalyzed Allylic Amination of Homoallylic Alcohols with Amines via Carbon-Carbon Bond Cleavage
Sun, Gui-Jun,Wang, Yong,Kang, Qiang
supporting information, p. 2931 - 2936 (2015/09/28)
An efficient approach for palladium(II) acetate catalyzed allylic amination of homoallylic alcohols with various amines via sequential retro-allylation and amination was developed, which afforded the corresponding allylic amines in up to 98% yield.
Identification of diarylsulfonamides as agonists of the free fatty acid receptor 4 (FFA4/GPR120)
Sparks, Steven M.,Chen, Grace,Collins, Jon L.,Danger, Dana,Dock, Steven T.,Jayawickreme, Channa,Jenkinson, Stephen,Laudeman, Christopher,Leesnitzer, M. Anthony,Liang, Xi,Maloney, Patrick,McCoy, David C.,Moncol, David,Rash, Vincent,Rimele, Thomas,Vulimiri, Padmaja,Way, James M.,Ross, Sean
, p. 3100 - 3103 (2014/06/24)
The exploration of a diarylsulfonamide series of free fatty acid receptor 4 (FFA4/GPR120) agonists is described. This work led to the identification of selective FFA4 agonist 8 (GSK137647A) and selective FFA4 antagonist 39. The in vitro profile of compounds 8 and 39 is presented herein.
Identification of diarylsulfonamides as agonists of the free fatty acid receptor 4 (FFA4/GPR120)
Sparks, Steven M.,Chen, Grace,Collins, Jon L.,Danger, Dana,Dock, Steven T.,Jayawickreme, Channa,Jenkinson, Stephen,Laudeman, Christopher,Leesnitzer, M. Anthony,Liang, Xi,Maloney, Patrick,McCoy, David C.,Moncol, David,Rash, Vincent,Rimele, Thomas,Vulimiri, Padmaja,Way, James M.,Ross, Sean
, p. 3100 - 3103 (2015/02/05)
The exploration of a diarylsulfonamide series of free fatty acid receptor 4 (FFA4/GPR120) agonists is described. This work led to the identification of selective FFA4 agonist 8 (GSK137647A) and selective FFA4 antagonist 39. The in vitro profile of compounds 8 and 39 is presented herein.
Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI
Alp, Cemalettin,?zsoy, ?eyda,Alp, Nurdan Alcan,Erdem, Deryanur,Gültekin, Mehmet Serdar,Küfrevio?lu, ?mer Irfan,?entürk, Murat,Supuran, Claudiu T.
, p. 818 - 824 (2013/02/23)
The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II and human serum isozyme VI, with a series of tosylited aromatic amine derivatives was investigated. The KI ranges of compounds 1-14 and acetazolamide against hCA I ranged between 1.130 and- 448.2 μM, against hCA II between 0.103 and- 14.3 μM, and against hCA VI ranged between 0.340 and- 42.39 μM. Tosylited aromatic amine derivatives are thus interesting hCA I, II and VI inhibitors, and might be used as leads for generating enzyme inhibitors eventually targeting other isoforms which have not been assayed yet for their interactions with such agents.
Half-sandwich scorpionates as nitrene transfer catalysts
Liang, Shengwen,Jensen, Michael P.
, p. 8055 - 8058 (2013/02/22)
Scorpionate complexes of the middle to late 3d transition metals [(L)M(NCMe)3](BF4)n (M = Mn, Fe, Co, Ni: 1 M, L = tris(3,5-dimethylpyrazol-1-yl)methane, TpmMe,Me, n = 2; 2M, L = tris(3-phenylpyrazol-1-yl)methane, TpmPh, n = 2; 3M except 3Mn, L = hydrotris(3,5-dimethylpyrazol-1-yl) borate, [TpMe,Me]-, n = 1; 4M, L = hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate, [TpPh,Me] -, n = 1) were examined as catalysts for styrene aziridination and THF amination using phenyl-N-tosyliodinane as a nitrene donor. [(Tpm Me,Me)Fe(NCMe)3](BF4)2 (1 Fe) was identified as the most active catalyst, giving nearly quantitative nitrene transfer yields at 5 mol % loadings. The reactivity of 1Fe with a wider range of organic substrates was also explored, and a striking observation was strong selectivity for aromatic rather than benzylic amination for alkylaromatic substrates.
A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates
Shekhar, Shashank,Dunn, Travis B.,Kotecki, Brian J.,Montavon, Donna K.,Cullen, Steven C.
, p. 4552 - 4563 (2011/07/31)
A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO 4 in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.
Transition metal complexes in the controlled synthesis of polyolefins substituted with functional groups
-
, (2008/06/13)
A method is provided for the polymerization of olefins substituted with a functional group using a transition metal catalyst that, by virtue of one or more stabilizing groups incorporated within the catalyst structure, “fixes” the stereoconfiguration of e
