cas 80-39-7, N-Ethyl-p-toluenesulfonamide | Articles data

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Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec
Sang, Dayong,Dong, Bingqian,Liu, Yunfeng,Tian, Juan
p. 3586 - 3595
(2022/02/25)

Nickel/Photoredox Dual Catalytic Cross-Coupling of Alkyl and Amidyl Radicals to Construct C(sp3)-N Bonds
The construction of C(sp3)-N bonds via direct radical-radical cross-coupling under benign conditions is a desirable but challenging approach. Herein, the cross-coupling of alkyl and amidyl radicals to build aliphatic C-N bonds in a concise, mild, and oxid
Zhou, Shaofang,Lv, Kang,Fu, Rui,Zhu, Changlei,Bao, Xiaoguang
p. 5026 - 5034
(2021/05/07)

Manganese-Catalyzed N-F Bond Activation for Hydroamination and Carboamination of Alkenes
A visible-light-promoted method for generating amidyl radicals from N-fluorosulfonamides via a manganese-catalyzed N-F bond activation strategy is reported. This protocol employs a simple manganese complex, Mn2(CO)10, as the precatalyst and a cheap silane, (MeO)3SiH, as both the hydrogen-atom donor and the F-atom acceptor, enabling intramolecular/intermolecular hydroaminations of alkenes, two-component carboamination of alkenes, and even three-component carboamination of alkenes. A wide range of valuable aliphatic sulfonamides can be readily prepared using these practical reactions.
Ji, Yun-Xing,Li, Jinxia,Li, Chun-Min,Qu, Shuanglin,Zhang, Bo
supporting information
p. 207 - 212
(2021/01/09)

Synthesis of N-substituted sulfonamides containing perhalopyridine moiety as bio-active candidates
A series of new halogenated aryl sulfonamides, as bio-active candidates, was synthesized from the reaction of the corresponding aryl sulfonamides with pentafluoro- and pentachloropyridines. Surprisingly, unlike aryl sulfonamides, the reaction of sulfamides with pentafluoro- and pentachloropyridines gave unexpected bis-perfluoro(chloro)pyridin-4-ylamines.
Hosseini, Raziyeh,Mohammadiannejad, Kazem,Ranjbar-Karimi, Reza
(2020/03/18)

Transition-Metal-Free One-Step Synthesis of Ynamides
A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
p. 4458 - 4466
(2019/03/26)

Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols
An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield).
Reed-Berendt, Benjamin G.,Morrill, Louis C.
p. 3715 - 3724
(2019/03/30)

Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis
We report a one-step procedure for the preparation of N-(2-pyrrole)-sulfonamides from sulfonamides and pyrroles. The reaction uses visible light, an acridinium dye as photocatalyst and oxygen as the terminal oxidant for the oxidative C-N bond formation; structures of several reaction products were confirmed by X-ray structure analysis. The reaction is selective for pyrroles, due to the available oxidation power of the photocatalyst and the required stability of the carbocation intermediate under the reaction conditions.
Meyer, Andreas Uwe,Berger, Anna Lucia,K?nig, Burkhard
supporting information
p. 10918 - 10921
(2016/09/09)

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation
The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).
Saidykhan, Amie,Ebert, Jenessa,Martin, William H.C.,Gallagher, Richard T.,Bowen, Richard D.
p. 165 - 173
(2016/11/09)

Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-NaI as the Electrolyte Solution at Room Temperature
With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.
Zhang, Chen,Chen, Yibin,Yuan, Gaoqing
p. 1277 - 1282
(2016/12/27)

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst
An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH4I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.
Jiang, Yang-Ye,Wang, Qing-Qing,Liang, Sen,Hu, Li-Ming,Little, R. Daniel,Zeng, Cheng-Chu
p. 4713 - 4719
(2016/07/06)

Copper-catalyzed trifluoromethylation and cyclization of aromatic-sulfonyl-group-tethered alkenes for the construction of 1,2-benzothiazinane dioxide type compounds
A multi-talented system: An efficient copper-catalyzed tandem trifluoromethylation/annulation of an electron-deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2-benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.
Dong, Xiang,Sang, Rui,Wang, Qiang,Tang, Xiang-Ying,Shi, Min
supporting information
p. 16910 - 16915
(2014/01/06)

Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 6102 - 6104
(2013/07/11)

Hydroamination of unactivated alkenes catalyzed by novel platinum(II) N -heterocyclic carbene complexes
Cationic platinum(II) complexes with bi- or tridentate (pincer) functionalized NHC ligands were found to be catalytically active in the hydroamination of unactivated alkenes. In some cases, the presence of water had an activating effect on the complexes. Reactions with the N-nucleophilic substrate morpholine led to a noncatalytic reaction in which the deprotonation product of the key cationic β-aminoalkyl platinum complex could be isolated and characterized. Surprisingly, attempted protonation of this complex did not give the expected N-alkylated product, indicating either the thermodynamic unfavorability of C-Pt bond cleavage or its kinetic inertness.
Cao, Peng,Cabrera, Jose,Padilla, Robin,Serra, Daniel,Rominger, Frank,Limbach, Michael
experimental part
p. 921 - 929
(2012/04/10)

TiCl4-mediated direct N-alkylation of sulfonamides with inactive ethers
A TiCl4-mediated intermolecular or intramolecular direct N-alkylation reaction of sulfonamides with inactive ethers as alkylating agents was successfully achieved. This method provides a novel approach towards N-alkyl sulfonamides from inactive ethers via an easy workup procedure. Georg Thieme Verlag Stuttgart · New York.
Chen, Jiayan,Dang, Ling,Li, Qiang,Ye, Yong,Fu, Shaomin,Zeng, Wei
supporting information; scheme or table
p. 595 - 600
(2012/03/27)

Directed ortho -metalation-cross-coupling strategies. One-pot Suzuki reaction to biaryl and heterobiaryl sulfonamides
A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 → 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls, 3 → 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.
Schneider, Cedric,Broda, Ellen,Snieckus, Victor
supporting information; experimental part
p. 3588 - 3591
(2011/10/03)

Efficient dehydrative C-N bond formation using alcohols and amides in the presence of silica supported perchloric acid as a heterogeneous catalyst
Silica supported perchloric acid has been utilized as an efficient heterogeneous recyclable catalyst for N-alkylation of amides (sulfonamides and carboxamides) using alcohols (primary and secondary aliphatic as well as benzylic). The products are formed in high yields within 2-3 h.
Das, Biswanath,Reddy, Parigi Raghavendar,Sudhakar, Chithaluri,Lingaiah, Maram
experimental part
p. 3521 - 3522
(2011/06/27)

Phosphotungstic acid catalyzed amidation of alcohols
Mild nucleophilic substitution reactions of benzhydrylic, benzylic, allylic, and simple aliphatic alcohols with sulfonamides, benzamide, and 4-nitroaniline in the presence of 12-phosphotungstic acid as an efficient, eco-friendly, cheap, and air- and moisture-tolerant catalyst for the construction of C-N bonds has been investigated. The amine derivatives were obtained in good yields (up to 98%). The reusable nature of the 12-phosphotungstic acid makes this protocol more attractive. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Wang, Guan-Wu,Shen, Ye-Bing,Wu, Xue-Liang
experimental part
p. 4367 - 4371
(2009/04/14)

New aspects of catalytic intramolecular C-H amination: Unexpected formation of a seven-membered ring in nitrogen-containing systems
The first example of the formation of a seven-membered ring by way of intramolecular-catalyzed amination of saturated C-H bonds is reported (Du Bois reaction). The influence of various structural parameters was studied, and it was shown that the unexpected regioselectivity observed in nitrogen-containing systems could be rationalized by conformational factors. These results open the way to innovative strategies for the general synthesis of polyfunctionalized piperidines.
Toumieux, Sylvestre,Compain, Philippe,Martin, Olivier R.,Selkti, Mohamed
p. 4493 - 4496
(2007/10/03)

Synthesis of phenyl arylsulfonyl-alkyl-dithiocarbamates and their hydrolytic reactivity in hydroxide and hydroperoxide media
Eight previously unreported phenyl arylsulfonyl-alkyl-dithiocarbamates were synthesized by treatment of arylsulfonamides with phenyl chlorodithioformate in an adaptation of a general amine acylation method. A kinetic investigation of their alkaline hydrolysis was performed and the experimental data are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Norberto, Fatima,Araujo, M. Eduarda M.,Santos, Lidia,Jaime, Marta S. P.,Mateus, Pedro M. V.,Herves, Pablo
p. 4710 - 4714
(2007/10/03)

Arenesulfonylheterocycles (I): Synthesis and reactions of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with amines
The direct sulfonylation of 4,5-dichloropyridazin-3-ones with some benzenesulfonyl chlorides in the presence of base in tetrahydrofuran gave only the corresponding N-sulfonylated product. The reaction of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with some aliphatic amines under neutral conditions afforded 5-alkylamino-2-benzenesulfonyl-4-chloropyridazin-3-ones and/or the corresponding N-alkyl-benzenesulfonamides.
Kweon, Deok-Heon,Kim, Ho-Kyun,Kim, Jeum-Jong,Chung, Hyun A.,Woo, Song Lee,Kim, Sung-Kyu,Yoon, Yong-Jin
p. 203 - 211
(2007/10/03)

Synthesis of a series of dichloroamino- and dihalosulfonamido-1,3,5-triazines and investigation of their hindered rotation and stereodynamic behaviour by NMR spectroscopy
Mono-substituted 1,3,5-triazines (s-triazines) have been prepared and characterised by NMR spectroscopy. The room temperature 13C NMR spectra of dichloroamino-s-triazines show three signals for the triazine ring, clearly indicating that C(2) and C(3) are in inequivalent environments. At elevated temperatures, two of the signals broaden and coalesce. Conversely, a number of dihalosulfonamido-s-triazine compounds were found to display only one signal for C(2) and C(3), indicating that the degree of π-bonding in the exocyclic C-N bond in these compounds is less significant. The low temperature exchange limits for the dihalosulfonamido-s-triazine compounds are reported.
Brewer, Stuart A.,Burnell, Helen T.,Holden, Ian,Jones, Brian G.,Willis, Colin R.
p. 1231 - 1234
(2007/10/03)

Indole Resin: A Versatile New Support for the Solid-Phase Synthesis of Organic Molecules
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Estep, Kimberly G.,Neipp, Christopher E.,Stephens Stramiello, Linda M.,Adam, Mavis D.,Allen, Martin P.,Robinson, Shaughnessy,Roskamp, Eric J.
p. 5300 - 5301
(2007/10/03)

Improved functionalized resin for chemical synthesis
A support functionalized by an indole or pyrrole aldehyde is useful for the solid phase synthesis of amide type compounds.
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(2008/06/13)

Tin for Organic Synthesis, 7. New Regioselective Syntheses of Diaryl Sulfones, Arenesulfonamides, and Arenesulfonic Acid Sodium Salts
The reaction of (trialkylstannyl)arenes 1 with corresponding reagents containing a chlorosulfonyl group leads, by exclusive ipso substitution, to important diaryl sulfones 2a - i, N-alkylarenesulfonamides 8a - f, and sodium arenesulfonates 13a - c in high yields under mild conditions.The specific leaving ability of the stannyl group allows, moreover, the preparation of arylsulfonyl isomers which are not accessible under the influence of the conventional directing forces of substituents.With N,N-dialkylamidosulfonyl chloride / AlCl3 complexes no destannylation takes place, but the first intramolecular sulfonyltin complex 11 is formed.This result is used to discuss details of the mechanism involved. Key Words: Aromatic substitution, electrophilic / Sulfones, synthesis of / Sulfonamides, synthesis of / Sulfonic acids, sodium salts, synthesis of/ Stannanes, trialkylaryl-, application of
Neumann, Wilhelm P.,Wicenec, Christian
p. 763 - 768
(2007/10/02)

Aromatic polycyclic derivatives, their process of preparation and their use in human and veterinary medicine and in cosmetics
An aromatic polycyclic compound has the formula STR1 wherein R represents --SO3 H, SO2 NHR3, STR2 --SO2 R3, --SOR3 or --SR3, R3 represents lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aminoalkyl, carboxyalkyl, aminocarboxyalkyl or alkoxyalkyl, R' represents hydrogen, lower alkyl, lower alkoxy, hydroxy, C1 -C4 acyloxy or amino, R" represents hydrogen, lower alkyl or lower alkoxy, or R' and R", taken together, form an oxo, methano or hydroxyimino radical, R1 represents hydrogen or lower alkyl, n is 0 or 1, when n=1, R2 represents hydrogen or lower alkyl, or R1 and R2, taken together form a vinylene radical, and Ar represents an aromatic radical selected from STR3 wherein R4, R5, R6, R7, R8, R9, R10 and R11 represent hydrogen or lower alkyl, at least one of R4 and/or R5 being other than hydrogen, and at least two of R8 -R11 being other than hydrogen, A represents methylene or dimethylene substituted or not by lower alkyl; when A represents dimethylene, R8 and R10 together can form a methylene or dimethylene radical, and the salts of the compound of formula I as well as their geometric and optical isomers. These compounds are useful in human and veterinary medicines and in cosmetic compositions.
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(2008/06/13)

Preparation of N-substituted arylsulfonamides
N-substituted arylsulfonamides which comprises the steps of (a) reacting an aryl hydrocarbon with chlorosulfonic acid to form a crude chlorosulfonation reaction product, (b) adding said crude reaction product to a mixture comprising an aliphatic amine, an alkali or alkaline earth metal hydroxide and water to form an amidation reaction mixture, (c) maintaining the temperature of the amidation reaction mixture at between about 50° C. and 100° C. and the pH at above about 7 with stirring for a period of time of up to about 2 hours, and optionally (d) separating the resulting N-substituted arylsulfonamide from the amidation reaction product.
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(2008/06/13)

NUCLEOPHILIC SUBSTITUTION AT SULFONYL SULFUR ATOM : AMINOLYSIS OF 1-TOSYL-3-METHYL IMIDAZOLIUM CHLORIDE IN AQUEOUS MEDIUM.
Kinetics of the reaction of 1-tosyl-3-methyl-imidazolium chloride with various amines were measured to examine the nature of sulfonyl transfer in enzymatic reactions.The activations parameters and the value of the Broensted exponent, β=0.48, are consistent with a small degree of bonding between the entering amine and the sulfur atom in the transition state.Similarities in the nucleophilic behavior of sulfonyl and carbonyl groups are detected.
Monjoint, Pierre,Ruasse, Marie-Francoise
p. 3183 - 3186
(2007/10/02)

Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation
The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
p. 721 - 725
(2007/10/02)