- Synthesis of Ferrocenesulfonyl Chloride: Key Intermediate toward Ferrocenesulfonamides
-
Ferrocenesulfonyl chloride is the key intermediate in the synthesis of ferrocenesulfonamides, a family of underexplored derivatives. A one-pot synthesis of this compound, able to easily deliver multigram quantities of product, is reported. An original protocol for the synthesis of ferrocenesulfonamides is described along with highlighting the reactivity difference between arene and ferrocenesulfonyl chlorides. Finally, an example of diastereoselective deprotolithiation of chiral ferrocenesulfonamides is described.
- Erb, William,Wen, Min,Roisnel, Thierry,Mongin, Florence
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p. 2612 - 2620
(2021/05/06)
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- Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates
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Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).
- Kornilova, T. A.,Nikitina, D. A.,Zenkevich, I. G.
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p. 1931 - 1941
(2021/09/15)
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- Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
-
An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.
- Fu, Ying,Wu, Qing-Kui,Du, Zhengyin
-
supporting information
p. 1896 - 1900
(2021/04/06)
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- Synthesis method of aryl tertiary sulfonamide compounds promoted by visible light
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The invention provides a synthesis method of aryl tertiary sulfonamide compounds promoted by visible light. In a non-protonic solvent, N-benzyl tertiary amine and arylsulfonyl chloride are used as rawmaterials, under the conditions of photosensitizer catalysis and illumination, a reaction is carried out for 1-4h at room temperature, and then separation and purification are carried out to obtain the product. The synthesis method of the aryl tertiary sulfonamide compound provided by the invention has the advantages of mild reaction conditions, simplicity and convenience in operation, short reaction time, no need of any transition metal catalysis and environmental friendliness.
- -
-
Paragraph 0019-0020
(2021/01/25)
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- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
-
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.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
-
-
- KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
-
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.
- Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
-
-
- Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate
-
A new method for the preparation of sulfonamides from sodium sulfinates and amines is developed. A stoichiometric amount of m-chloroperbenzoic acid as oxidant and a catalytic amount of 1-iodopropane provides the corresponding sulfonamides in good yields under mild reaction conditions. In this protocol, 1-iodopropane is first oxidized by m-chloroperbenzoic acid into the corresponding hypervalent iodine intermediate iodosylpropane, which is highly unstable and decomposes at once to form hypoiodous acid. Then, the following reaction of the generated active hypoiodous acid with sodium sulfinates and amines results in the corresponding sulfonamides.
- Zhou, Zhongshi,He, Xuehan
-
supporting information
p. 280 - 284
(2019/11/16)
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- Synthesis method of aryl tertiary sulfonamide compound
-
The invention provides a synthesis method of an aryl tertiary sulfonamide compound. In an aprotic solvent, with aryl sulfonyl chloride and a N,N-disubstituted-4-oxopiperidine quaternary ammonium saltcompound as raw materials and N-methylmorpholine as alka
- -
-
Paragraph 0026; 0027
(2019/10/01)
-
- Double C-N bond cleavages of: N-alkyl 4-oxopiperidinium salts: Access to unsymmetrical tertiary sulfonamides
-
In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- A nd oxidant-free conditions.
- Fu, Ying,Li, Ming-Peng,Shi, Chun-Zhao,Li, Fang-Rong,Du, Zhengyin,Huo, Congde
-
supporting information
p. 10172 - 10177
(2019/12/26)
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- Hypervalent Iodine Mediated Sulfonamide Synthesis
-
A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
- Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
-
supporting information
p. 2695 - 2701
(2019/04/08)
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- KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides
-
KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.
- Zhang, Zhang,Liu, Yong-Hong,Zhang, Xi,Wang, Xi-Cun
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p. 2763 - 2770
(2019/04/10)
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- Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
-
Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.
- Gui, Jiao,Xie, Haisheng,Jiang, Huanfeng,Zeng, Wei
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p. 2804 - 2807
(2019/04/30)
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- Aryl sulfonamide tertiary amine compound synthesizing method
-
The invention provides an aryl sulfonamide tertiary amine compound synthesizing method. According to the method, in an anhydrous aprotic solvent and under nitrogen protection, acryl sulfonyl chlorideand di-tertiary amine react for 1 to 12 hours according to a molar ratio of (1 to 1) to (1 to 20) under the condition of 50 to 150 DEG C, and the aryl sulfonamide tertiary amine compound can be obtained by purification. According to the method disclosed by the invention, the acryl sulfonyl chloride and the di-tertiary amine can directly generate C-S bond formation in the aprotic solvent and generate C-N bond breakage at the same time. According to the one-step aryl sulfonamide synthesizing method, raw materials are easy to obtain, a synthesizing technology is simple, operation is convenient, cost is low, and yield is high.
- -
-
Paragraph 0015
(2018/05/16)
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- Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines
-
A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).
- Fu, Ying,Xu, Qin-Shan,Shi, Chun-Zhao,Du, Zhengyin,Xiao, Caiqin
-
supporting information
p. 3502 - 3506
(2018/09/14)
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- Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides
-
By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.
- Bao, Xiaodong,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Liang, Guang,Xia, Qinqin
-
supporting information
p. 2853 - 2858
(2018/06/25)
-
- Preparation method for sulfonamide compound
-
The invention discloses a preparation method for a sulfonamide compound. The preparation method comprises the following steps: with NIS as an oxidizing agent and potassium tert-butoxide as a base, reacting formamide with sodium arylsulfinate in an organic solvent, and carrying out post-treatment after the reaction is completed so as to obtain the sulfonamide compound. The preparation method uses formamide and sodium arylsulfinate as substrates for synthesis of the sulfonamide compound; the raw materials for the reaction are cheap and easily available; and the preparation method is simple.
- -
-
Paragraph 0137; 0138; 0139; 0140; 0141; 0142
(2017/12/14)
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- An approach to C-N activation: Coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with: Tert -amines via a metal-, oxidant- and halogen-free anodic oxidation
-
tert-Amines were harnessed to afford arenesulfonyl hydrazides and arenesulfonyl chlorides via a metal-, oxidant- and halogen-free electrochemical oxidative coupling in an undivided cell at RT. This environmentally benign approach afforded a wide spectrum of sulfonamides in satisfactory yields using cheap and renewable Pencil Graphite Electrodes (PGEs).
- Sheykhan,Khani,Abbasnia,Shaabanzadeh,Joafshan
-
supporting information
p. 5940 - 5948
(2017/12/26)
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- Eosin Y-Sensitized Photocatalytic Reaction of Tertiary Aliphatic Amines with Arenesulfonyl Chlorides under Visible-Light Irradiation
-
A mild, practical, and environmentally friendly route to vinyl sulfones and sulfonamides has been developed based on the reaction of aliphatic amines with arenesulfonyl chlorides in the presence of eosin Y as a photocatalyst under visible light. The method permits the selective formation of vinyl sulfones or sulfonamides, depending on the oxidation environment and solvent. A wide range of products were obtained in moderate to good yields under the optimized conditions.
- Cai, Yuguo,Zhang, Ronghua,Sun, Deli,Xu, Song,Zhou, Qiguang
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p. 1630 - 1635
(2017/08/11)
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- Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines
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The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides.
- Taniguchi, Nobukazu
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p. 2030 - 2035
(2017/03/17)
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- Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion
-
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.
- Jagadale, Megha,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 125 - 131
(2016/02/14)
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- I2/TBHP Mediated C-N and C-H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction
-
A novel method toward synthesis of sulfonamides and β-arylsulfonyl enamines has been developed via I2/TBHP mediated C-N and C-H bond cleavage of tertiary amines, which features highly selective formation of two different target products depending on the reaction solvent. The experimental results reveal that H2O as the solvent could effectively achieve the C-N bond cleavage to produce sulfonamides due to H2O participating in the reaction process where H2O plays a dual role. Differing from H2O, organic solvents (such as dimethyl sulfoxide) could promote the C-H bond cleavage of tertiary amines to yield β-arylsulfonyl enamines.
- Lai, Junyi,Chang, Liming,Yuan, Gaoqing
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p. 3194 - 3197
(2016/07/14)
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- DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents
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Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.
- Jones, Caroline S.,Bull, Steven D.,Williams, Jonathan M. J.
-
supporting information
p. 8452 - 8456
(2016/09/28)
-
- Synthesis of sulfonamides: Via copper-catalyzed oxidative C-N bond cleavage of tertiary amines
-
A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C-N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.
- Ji, Jing,Liu, Zhengyi,Liu, Ping,Sun, Peipei
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p. 7018 - 7023
(2016/07/30)
-
- Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
-
A novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described. This method involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant. This protocol does not require purification techniques such as column chromatography and recrystalization.
- Parumala, Santosh Kumar Reddy,Peddinti, Rama Krishna
-
supporting information
p. 1232 - 1235
(2016/03/01)
-
- Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines
-
An efficient electrochemical synthesis of sulfonamides (yields 56–98%) from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines was performed in an undivided cell with graphite anode and iron cathode in MeCN–H2O medium using halides as redox mediators and supporting electrolytes.
- Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Syroeshkin, Mikhail A.,Glinushkin, Alexey P.,Nikishin, Gennady I.
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p. 538 - 539
(2016/12/02)
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- NH4I-Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines
-
A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper. Sulfonimides were synthesized through the oxidation coupling of arylsufonylhydrazides and amines by TBHP/NH4I system in moderate to good yields.
- Yu, Hui,Zhang, Yonghao
-
supporting information
p. 359 - 362
(2016/04/26)
-
- One-Pot Synthesis of Sulfonamides from Sodium Sulfinates and Amines via Sulfonyl Bromides
-
a new and convenient procedure has been developed for the preparation of sulfonamides from sodium sulfinates and amines with (n-C4H9)4NBr as bromine source and m-chloroperbenzoic acid as oxidant. This S-N bond formation reaction proceeds efficiently via sulfonyl bromides under neutral conditions to afford the corresponding sulfonamides in good yields at room temperature.
- Wu, Sixue,Zhang, Yikun,Zhu, Min,Yan, Jie
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p. 2699 - 2704
(2016/11/30)
-
- 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
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p. 4713 - 4719
(2016/07/06)
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- Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
-
(Chemical Equation Presented). An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.
- Chow, Shiao Y.,Stevens, Marc Y.,Odell, Luke R.
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p. 2681 - 2691
(2016/04/26)
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- Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
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A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.
- Yotphan, Sirilata,Sumunnee, Ladawan,Beukeaw, Danupat,Buathongjan, Chonchanok,Reutrakul, Vichai
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p. 590 - 597
(2016/01/12)
-
- A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
-
Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure.
- Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
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p. 1703 - 1714
(2015/09/15)
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- Iodine-catalyzed oxidative amination of sodium sulfinates: A convenient approach to the synthesis of sulfonamides under mild conditions
-
The iodine-catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines canbe employed as the amine sources in this transformation. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. This transition-metalfree protocol offers an alternative and convenient approach for a preparation of a series of sulfonamides in moderate to good yields under mild conditions.
- Buathongjan, Chonchanok,Beukeaw, Danupat,Yotphan, Sirilata
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p. 1575 - 1582
(2015/03/04)
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- Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature
-
An efficient I2-mediated approach for the synthesis of sulfonamides at room temperature using water as the solvent has been developed. This method for the synthesis of sulfonamides is quite convenient and environmentally friendly. In addition, the purification procedure of the desired products becomes very easy. This journal is
- Pan, Xiaojun,Gao, Jian,Liu, Juan,Lai, Junyi,Jiang, Huanfeng,Yuan, Gaoqing
-
supporting information
p. 1400 - 1403
(2015/03/18)
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- Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
-
Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.
- Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 9513 - 9516
(2014/08/18)
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- Metal-free oxidative coupling of amines with sodium sulfinates: A mild access to sulfonamides
-
A practical and mild procedure for the preparation of sulfonamides through TBAI-catalyzed oxidative coupling of amines with sodium sulfinates using TBHP as an oxidant was presented. A variety of amines and sodium sulfinates could go through the transformation, without impacting the hydroxyl group. This journal is
- Zhao, Jinwu,Xu, Jingxiu,Chen, Jiaxi,Wang, Xiaoqin,He, Minghua
-
p. 64698 - 64701
(2015/04/27)
-
- Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
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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)
-
- Two-step route to indoles and analogues from haloarenes: A variation on the Fischer indole synthesis
-
In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehy
- Inman, Martyn,Carbone, Anna,Moody, Christopher J.
-
experimental part
p. 1217 - 1232
(2012/03/26)
-
- 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)
-
- DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
-
The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
- Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
-
supporting information; experimental part
p. 4876 - 4878
(2011/12/05)
-
- 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
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supporting information; experimental part
p. 3588 - 3591
(2011/10/03)
-
- Mild and general method for the synthesis of sulfonamides
-
Reaction of methyl sulfinates with lithium amides followed by 3-chloroperoxybenzoic acid oxidation of the resulting sulfinamides provides primary, secondary, and tertiary alkane-, arene-and heteroarenesulfonamides in high yields. This constitutes a mild and facile experimental protocol that avoids the use of hazardous, unstable, or volatile reagents and does not affect the configurational stability of the amines. Georg Thieme Verlag Stuttgart.
- Garcia Ruano, Jose Luis,Parra, Alejandro,Yuste, Francisco,Mastranzo, Virginia M.
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p. 311 - 319
(2008/12/22)
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- Expedient synthesis of sulfinamides from sulfonyl chlorides
-
Sulfinamides were synthesized from sulfonyl chlorides using a procedure involving in situ reduction of sulfonyl chlorides. The reaction is broad in scope and easy to perform.
- Harmata, Michael,Zheng, Pinguan,Huang, Chaofeng,Gomes, Maria G.,Ying, Weijiang,Ranyanil, Kanok-On,Balan, Gayatri,Calkins, Nathan L.
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p. 683 - 685
(2007/10/03)
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- PROCESS FOR MAKING SUBSTITUTED ARYL SULFONAMIDES USING AN INDIUM BASED CATALYST SYSTEM
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A process for making substituted aryl sulfonamides by sulfamoylation of an activated aromatic compound using an indium compound as a catalyst.
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- Reactivity of cage-like amines toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile
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The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25°C is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.
- Sadovskii,Solomoichenko,Kas'yan,Golodaeva,Anikanova,Kas'yan,Savelova
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- Oxidation of aromatic and aliphatic triisopropylsilanylsulfanyls to sulfonyl chlorides: Preparation of sulfonamides
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A series of aromatic and aliphatic triisopropylsilanylsulfanyls were prepared and oxidized to the sulfonyl chlorides with KNO3/SO 2Cl2. The sulfonyl chlorides were characterized via their conversion to sulfonamides.
- Gareau, Yves,Pellicelli, Jonathan,Laliberté, Sébastien,Gauvreau, Danny
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p. 7821 - 7824
(2007/10/03)
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- Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides
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A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.
- Pandya, Rina,Murashima, Takashi,Tedeschi, Livio,Barrett, Anthony G. M.
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p. 8274 - 8276
(2007/10/03)
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- Arenesulfonylheterocycles (I): Synthesis and reactions of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with amines
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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
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p. 203 - 211
(2007/10/03)
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- Catalytic arylation of sulfamoyl chlorides: A practical synthesis of sulfonamides
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Commercially available indium(III) triflate is shown to be an efficient catalyst for the sulfamoylation of aromatics.
- Frost, Christopher G.,Hartley, Joseph P.,Griffin, David
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p. 1928 - 1930
(2007/10/03)
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- Heck reactions of 3-iodo-N-methyl-quinolin-2(1H)-ones with 2-methylbut-3-en-2-ol
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Treatment of 4-acetoxy-3-iod-N-methyl-quinolin-2(1H)-one, 3-iod-N-methyl-4-tosyloxy-quinolin-2(1H)-one and 3-iod-4-methoxy-N-methyl-quinolin-2(1H)-one with 2-methylbut-3-en-2-ol under Heck conditions led to the related (E)-3-(3-methylbut-1-en-3-olyl)-derivatives, potential precursors of dimeric quinolines. Dehydration of the tertiary hydroxy group of 4-methoxy-(E)-3-(3-methylbut-1-en-3-olyl)-N-methyl-quinolin-2(1H)-one with acetic acid gave 4-methoxy-(E)-3-(3-methylbut-1,3-dienyl)-N-methyl-quinolin-2(1H)-one.
- Reisch,Iding
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p. 579 - 582
(2007/10/02)
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