21226-32-4Relevant articles and documents
Sequential C-S and S-N Coupling Approach to Sulfonamides
Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 1841 - 1845 (2020/03/04)
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization
Kikkawa, Shoko,Masu, Hyuma,Katagiri, Kosuke,Okayasu, Misaki,Yamaguchi, Kentaro,Danjo, Hiroshi,Kawahata, Masatoshi,Tominaga, Masahide,Sei, Yoshihisa,Hikawa, Hidemasa,Azumaya, Isao
, p. 2936 - 2946 (2019/05/10)
N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.
Selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis
Wang, Jingjing,Li, Feng,Pei, Wenlong,Yang, Mixue,Wu, Yidan,Ma, Danyang,Zhang, Furong,Wang, Jianhui
supporting information, p. 1902 - 1905 (2018/04/19)
The selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis is described. The reaction tolerates a broad range of functional groups, and the desired products were obtained in 10–95% yield.
Copper-catalyzed N-arylation of sulfonamides with boronic acids in water under ligand-free and aerobic conditions
Nasrollahzadeh, Mahmoud,Ehsani, Ali,Maham, Mehdi
, p. 505 - 508 (2014/03/21)
An efficient and novel method for the copper-catalyzed arylation of sulfonamides in water under ligand-free conditions is reported. The significant advantages of this methodology are high yields, simple workup procedure, and elimination of toxic materials
Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions
Wang, Xiang,Guram, Anil,Ronk, Michael,Milne, Jacqueline E.,Tedrow, Jason S.,Faul, Margaret M.
supporting information; experimental part, p. 7 - 10 (2012/01/06)
This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole.
Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
experimental part, p. 143 - 148 (2010/11/16)
An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.
Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands
Deng, Wei,Liu, Lei,Zhang, Chen,Liu, Min,Guo, Qing-Xiang
, p. 7295 - 7298 (2007/10/03)
A highly general, convenient, and inexpensive catalyst system was developed for the N-arylation of sulfonamides with aryl iodides or bromides by using 5-20 mol % of CuI as catalyst, 20 mol % of N-methylglycine (for aryl iodides) or N,N-dimethylglycine (for aryl bromides) as ligand, and K3PO 4 as base.
Palladium-catalyzed amination of aryl bromides and aryl triflates using diphosphane ligands: A kinetic study
Guari, Yannick,Van Strijdonck, Gino P. F.,Boele, Maarten D. K.,Reek, Joost N. H.,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.
, p. 475 - 482 (2007/10/03)
[Pd(P-O-P)(Ar)]+ complexes with ligands that have wide bite angles are active catalysts for the coupling of aniline derivatives with aryl triflates. Kinetic studies show that for these systems a fast equilibrium that involves coordination of the amine precedes the deprotonation, which is the rate-limiting step of the reaction. This reaction is faster for compounds with a smaller P-Pd-P angle. When halide salts are present, the base sodium tert-butoxide is activated and adds to the palladium complex. This rate-limiting step is preceded by a fast equilibrium that involves decoordination of the halide. The initial reaction rate is faster for compounds with a larger P-Pd-P angle. This is due to the closer proximity of the oxygen to the Pd center, and this assists in the dissociation of the halide.
Ortho effect in dissociation of substituted N-phenylbenzenesulfonamides
Nadvornik, Jiri,Ludwig, Miroslav
, p. 1380 - 1392 (2007/10/03)
Twenty-five 2,2′-disubstituted N-phenylbenzenesulfonamides (2-X-C6H4SO2NHC6H4-Y-Z′) were synthesised and their purity checked by elemental analysis. This set of model substrates involved all possible combinations of methoxy, methyl, hydrogen, chloro, and nitro substituents. The dissociation constants of the sulfonamides were determined by potentiometric titration in methanol, pyridine, dimethyl sulfoxide, N,N-dimethylformamide, acetone, and acetonitrile. The dissociation constants pKHA obtained were correlated with various sets of substituent constants describing electronic and steric effects of the substituents, and the statistically treated data were used to discuss the contribution of the substituent effects in the dissociation and the difference between the effects transmitted from the two rings. A linear regression model explaining 99% of the variability of experimental data in all the solvents has been found and discussed. Moreover, the experimental data were also interpreted by the methods using latent variables, the principal component analysis (PCA) and conjugated deviation analysis (CDA), and two latent variables were shown to be statistically significant in the description of dissociation. The first obviously describes common action of electronic and steric effects of substituents; the other probably concerns a combined effect of substituent and solvent on the position of acid-base equilibrium.
Selective monodesulfonylation of N,N-disulfonylarylamines with tetrabutylammonium fluoride
Yasuhara, Akito,Kameda, Mitsuyoshi,Sakamoto, Takao
, p. 809 - 812 (2007/10/03)
The monodesulfonylation reaction of N,N-bis(methylsulfonyl)-, N,N- bis(phenylsulfonyl)-, and N,N-bis(p-tolylsulfonyl)arylamines easily proceeded using tetrabutylammonium fluoride in tetrahydrofuran under mild conditions to give the corresponding N-monosulfonylarylamines in excellent yields.
