6295-94-9Relevant articles and documents
High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides
Becica, Joseph,Hruszkewycz, Damian P.,Steves, Janelle E.,Elward, Jennifer M.,Leitch, David C.,Dobereiner, Graham E.
, p. 8981 - 8986 (2019)
Through targeted high-throughput experimentation (HTE), we have identified the Pd/AdBippyPhos catalyst system as an effective and general method to construct densely functionalized N,N-diaryl sulfonamide motifs relevant to medicinal chemistry. AdBippyPhos is particularly effective for the installation of heteroaromatic groups. Computational steric parametrization of the investigated ligands reveals the potential importance of remote steric demand, where a large cone angle combined with an accessible Pd center is correlated to successful catalysts for C-N coupling reactions.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
A red-emissive two-photon fluorescent probe for mitochondrial sodium ions in live tissue
Cho, Myoung Ki,Je, Jong Tae,Juvekar, Vinayak,Kang, Hyuk,Kim, Hwan Myung,Lee, Dong Joon,Lee, Hyo Won,Song, Ju Man
supporting information, p. 8929 - 8932 (2021/09/10)
A cyclocyanine (CC)-based organic small molecule two-photon (TP) fluorescent probe (CCNa1) was developed for mitochondrial sodium ion sensing.CCNa1exhibits a low solvatochromic shift and strong TP fluorescence enhancement at 575 nm upon binding to Na
Iridium complex-linked porous organic polymers for recyclable, broad-scope photocatalysis of organic transformations
Xu, Zi-Yue,Luo, Yi,Zhang, Dan-Wei,Wang, Hui,Sun, Xing-Wen,Li, Zhan-Ting
supporting information, p. 136 - 143 (2020/01/21)
Two rigid porous organic polymers (Ir-POP-1 and Ir-POP-2) were prepared from the coupling reactions of tetraphenylmethane tetraborate and two [Ir(ppy)2(dtbbpy)]+-based bitopic linkers and applied as heterogeneous visible-light photocatalysts for organic transformations. Ir-POP-2 was found to exhibit high catalytic activity for a wide range of organic reactions, which include Smiles-Truce rearrangement of alkyliodides, desulfurative conjugate addition to Michael acceptors, and aerobic oxidations of sulfides and arylboronic acids. For all the transformations, Ir-POP-2 could achieve heterogeneous photocatalytic efficiency that rivals that of the homogeneous prototype iridium complexes. This remarkably high photocatalytic performance has been attributed to the large pore size of the conjugated backbone. The new heterogeneous photocatalyst was also highly stable to achieve good recyclability for all the studied reactions and could be reused eight to nineteen times.
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.
Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature
Ouyang, Banlai,Liu, Deming,Xia, Kejian,Zheng, Yanxia,Mei, Hongxin,Qiu, Guanyinsheng
supporting information, p. 111 - 115 (2017/12/27)
A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.
Visible Light Mediated Aryl Migration by Homolytic C?N Cleavage of Aryl Amines
Alpers, Dirk,Cole, Kevin P.,Stephenson, Corey R. J.
supporting information, p. 12167 - 12170 (2018/09/11)
The photocatalytic preparation of aminoalkylated heteroarenes from haloalkylamides via a 1,4-aryl migration from nitrogen to carbon, conceptually analogous to a radical Smiles rearrangement, is reported. This method enables the substitution of amino group
CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature
Loukrakpam, Dineshwori Chanu,Phukan, Prodeep
supporting information, p. 4855 - 4858 (2017/11/29)
An expeditious protocol for amidation arylboronic acid has been developed using TsNBr2 as the nitrogen source in presence of a CuI as catalyst. Various arylboronic acids could be transformed into corresponding N-arylsulfonamide derivatives within a very short time using CuI as catalyst in presence of DBU at room temperature.
A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling reaction of sulfonyl azides with arylboronic acids leading to: N -arylsulfonamides
You, Chongren,Yao, Fang,Yan, Tao,Cai, Mingzhong
, p. 43605 - 43612 (2016/05/24)
A heterogeneous Chan-Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily available and inexpensive reagents, and recovered by simple filtration of the reaction solution and recycled at least 8 times without any decreases in activity.
Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion
Jagadale, Megha,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
, p. 125 - 131 (2016/02/14)
A silica-supported ionic liquid phase catalyst containing Keggin-type anion has been prepared by covalent grafting of ferrocene-tagged ionic liquid in a matrix of silica followed by anion metathesis reaction. This novel catalyst served as a robust heterogeneous catalyst for the synthesis of biologically active sulfonamides from 4-toluenesulfonyl chloride and amines. Additionally, recycling experiments showed that the catalyst could be reused five times.
