107491-54-3Relevant articles and documents
A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
Meshram,Patil, Vishvanath D.
, p. 1117 - 1121 (2009)
Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive feature of this method.
Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation
Ye, Fei,Berger, Florian,Jia, Hao,Ford, Joseph,Wortman, Alan,B?rgel, Jonas,Genicot, Christophe,Ritter, Tobias
, p. 14615 - 14619 (2019)
Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Herein, we report the first photoredox-catalyzed cross-coupling of aryl thianthrenium salts with a copper-based trifluoromethyl reagent, which enables a site-selective late-stage trifluoromethylation of arenes. The reaction proceeds with broad functional group tolerance, even for complex small molecules on gram scale. The method was further extended to produce pentafluoroethylated derivatives.
KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
, (2020)
A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.
Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base
Sharma, Ashwani Kumar,Das, Saibal Kumar
, p. 3807 - 3819 (2004)
Microwave-induced syntheses of sulfonamides, without using base under solvent-free conditions, have been developed. The process finds its utility because of its simple operational procedure and high yields. Moreover, the process is fast and accommodative to different substituents on aromatic as well as heteroaromatic rings rendering sulfonamides (28 examples).
Mild and efficient indium metal catalyzed synthesis of sulfonamides and sulfonic esters
Kim, Joong-Gon,Doo, Ok Jang
, p. 2501 - 2504 (2007)
A facile and efficient method for synthesizing sulfonamides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols. Georg Thieme Verlag Stuttgart.
Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
Hajiloo Shayegan, Mojtaba,Li, Zhong-Yuan,Cui, Xin
supporting information, (2021/12/02)
Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.
Carbon dot/TiO2nanocomposites as photocatalysts for metallaphotocatalytic carbon-heteroatom cross-couplings
Delbianco, Martina,Pieber, Bartholom?us,Reischauer, Susanne,Zhao, Zhouxiang
supporting information, p. 4524 - 4530 (2021/06/30)
Carbon dots have been previosly immobilized on titanium dioxide to generate photocatalysts for pollutant degradation and water splitting. Here we demonstrate that these nanocomposites are valuable photocatalysts for metallaphotocatalytic carbon-heteroatom cross-couplings. These sustainable materials show a large applicability, high photostability, excellent reusability, and broadly absorb across the visible-light spectrum.
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.
Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
Ouyang, Banlai,Zheng, Yanxia,Liu, Yi,Liu, Fei,Yao, Juying,Peng, Yiyuan
, p. 3694 - 3698 (2018/09/14)
A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.
Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
supporting information, p. 4161 - 4167 (2018/09/21)
In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
