312-63-0Relevant academic research and scientific papers
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.
Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
supporting information, p. 13481 - 13494 (2020/12/15)
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
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Paragraph 0052-0056, (2019/11/12)
The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.
Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
Dong, Wanrong,Liu, Chaoyang,Ma, Xinchi,Zhang, Yingjun,Peng, Zhihong,Xie, Dexun,An, Delie
, p. 3886 - 3893 (2019/06/18)
A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.
Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates
Zhao, Zijian,Lian, Yan,Zhao, Chang,Wang, Bing
supporting information, p. 1436 - 1442 (2018/06/01)
A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance (25 examples).
Method for ultrasound-assisted synthesis of N-arylsulfonamide
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Paragraph 0131; 0132; 0133, (2018/11/27)
The invention discloses a method for ultrasound-assisted synthesis of N-arylsulfonamide. N-arylsulfonamide compound is synthesized by series reaction of nitro reduction/sulfonyl chloride reduction/sulfonamidation with taking aromatic nitro compounds, sulfonyl chloride and iron powder as raw materials under ultrasonic stirring conditions. Water is used as a reaction medium and a hydrogen source inthe reaction. The method has the advantages of cheap and easily obtained raw materials, simple and mild reaction conditions, environmental friendliness, saving energy, high reaction selectivity and high yield, excellent compatibility of substrate functional groups and high application value.
Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature
Wei, Wei,Liu, Chunli,Yang, Daoshan,Wen, Jiangwei,You, Jinmao,Wang, Hua
supporting information, p. 987 - 992 (2015/03/30)
A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).
Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
supporting information, p. 1395 - 1399 (2015/03/18)
A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
Oxidative fluorination of N-arylsulfonamides
Buckingham, Faye,Calderwood, Samuel,Checa, Bego?a,Keller, Thomas,Tredwell, Matthew,Collier, Thomas Lee,Newington, Ian M.,Bhalla, Rajiv,Glaser, Matthias,Gouverneur, Véronique
, p. 33 - 39 (2015/09/22)
We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.
Cu(OAc)2-catalyzed N-arylation of sulfonamides with arylboronic acids or trimethoxy(phenyl)silane
Pan, Changduo,Cheng, Jiang,Wu, Huayue,Ding, Jinchang,Liu, Miaochang
experimental part, p. 2082 - 2092 (2009/10/17)
Cu(OAc)2-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20mol% of Cu(OAc)2, providing N-arylation products with yields ranging from moderate to good.
