35088-87-0Relevant academic research and scientific papers
S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling
Wang, Xuefeng,Yang, Min,Ye, Shengqing,Kuang, Yunyan,Wu, Jie
, p. 6437 - 6441 (2021/05/19)
Sulfuric chloride is used as the source of the -SO2- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. This journal is
AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST
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Paragraph 0033-0037; 0039-0054; 0066-0069; 0142-0143, (2021/04/06)
The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.
Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand
Chung Leung, Gulice Yiu,Ramalingam, Balamurugan,Loh, Gabriel,Chen, Anqi
, p. 546 - 554 (2020/04/22)
A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.
Hypervalent Iodine Mediated Sulfonamide Synthesis
Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
, p. 2695 - 2701 (2019/04/08)
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.
Iodine-catalyzed sulfonylation of sulfonyl hydrazides with: Tert -amines: A green and efficient protocol for the synthesis of sulfonamides
Chen, Jinyang,Han, Xiaoran,Mei, Lan,Liu, Jinchuan,Du, Kui,Cao, Tuanwu,Li, Qiang
, p. 31212 - 31216 (2019/10/19)
This study provides a direct, sustainable and eco-friendly method for the synthesis of various sulfonamides via the sulfonylation of sulfonyl hydrazides with tert-amines. The method utilizes sulfonyl hydrazides to oxidize and couple with tertiary amines through selective cleavage of C-N bonds. In this reaction, molecular iodine was used as the catalyst and t-butyl hydroperoxide was used as the oxidant.
Visible-light mediated sulfonylation of thiols via insertion of sulfur dioxide
Nair, Akshay M.,Kumar, Shreemoyee,Halder, Indranil,Volla, Chandra M. R.
, p. 5897 - 5901 (2019/06/24)
A simple and efficient visible-light mediated synthesis of thiosulfonates via a radical-radical coupling of sulfenyl radicals and arylsulfonyl radicals was developed. The reaction of thiols, aryldiazonium tetrafluoroborates and DABSO proceeded at room temperature using 5 mol% eosin Y. The reaction displayed wide functional group tolerance and delivered the unsymmetrical thiosulfonates in good to excellent yields.
TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines
Jiang, Hongmei,Tang, Xiaoyue,Xu, Zhihui,Wang, Huixian,Han, Kang,Yang, Xiaolan,Zhou, Yuanyuan,Feng, Yong-Lai,Yu, Xian-Yong,Gui, Qingwen
, p. 2715 - 2720 (2019/03/12)
A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C-N and C-H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity.
Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines
Chung, Sohyun,Kim, Jinho
supporting information, p. 792 - 795 (2019/02/16)
An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.
Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines
Zhang, Feng,Zheng, Danqing,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
supporting information, p. 1167 - 1170 (2018/02/23)
A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.
Method for synthesizing benzenesulfonamide compound by using benzenesulfonyl chloride compound and secondary amine through metal-free catalysis
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Paragraph 0025; 0026; 0027, (2019/01/08)
The invention provides a method for synthesizing a benzenesulfonamide compound by using a benzenesulfonyl chloride compound and secondary amine through metal-free catalysis. The method comprises the following steps: taking the benzenesulfonamide compound
