cas 22771-99-9, 4-(4-Chlorophenylsulfonyl)Morpholine, 97%

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S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling
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
Wang, Xuefeng,Yang, Min,Ye, Shengqing,Kuang, Yunyan,Wu, Jie
p. 6437 - 6441
(2021/05/19)

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST
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.
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Paragraph 0033-0037; 0039-0054; 0066-0069; 0148-0149

(2021/04/06)

Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand
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.
Chung Leung, Gulice Yiu,Ramalingam, Balamurugan,Loh, Gabriel,Chen, Anqi
p. 546 - 554
(2020/04/22)

Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO
We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
Lo, Pui Kin Tony,Chen, Yiding,Willis, Michael C.
p. 10668 - 10673
(2019/11/11)

Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines
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.
Chung, Sohyun,Kim, Jinho
supporting information
p. 792 - 795
(2019/02/16)

Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides
First introduced into medicines in the 1930s, the sulfonamide functional group continues to be present in a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity in the design of modern bioactive molecules, the underpinning methods for sulfonamide synthesis are essentially unchanged since their introduction, and rely on the use of starting materials with preinstalled sulfur-functionality. Herein we report a direct single-step synthesis of sulfonamides that combines two of the largest monomer sets available in discovery chemistry, (hetero)aryl boronic acids and amines, along with sulfur dioxide, using a Cu(II) catalyst, to deliver a broad range of sulfonamides. Sulfur dioxide is provided by the surrogate reagent DABSO. The reaction tolerates broad variation in both coupling partners, including aryl, heteroaryl and alkenyl boronic acids, as well as cyclic and acyclic alkyl secondary amines, and primary anilines. We validate the method by showing that a variety of drugs, and drug-fragments, can be incorporated into the process.
Chen, Yiding,Murray, Philip R. D.,Davies, Alyn T.,Willis, Michael C.
supporting information
p. 8781 - 8787
(2018/07/29)

Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines
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.
Zhang, Feng,Zheng, Danqing,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
supporting information
p. 1167 - 1170
(2018/02/23)

MANUFACTURING METHOD OF COMPOUND HAVING SULFONYL GROUP
The present invention relates to a method for manufacturing a compound having a sulfonyl group, which includes a step for reacting thiosulfonates in a solvent comprising nucleophilic bases with an electrophilic agent. Accordingly, the present invention can manufacture the compound having the sulfonyl group with a variety of structures with high efficiency and high yield through more simplified processes than conventional methods.COPYRIGHT KIPO 2018
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Paragraph 0187; 0188; 0190-0193

(2018/10/03)

Metal-free I2O5-mediated direct construction of sulfonamides from thiols and amines
A simple and convenient method has been developed for the construction of sulfonamides via I2O5-mediated sulfonylation of amines with arylthiols. The present protocol provides an attractive approach to sulfonamides in moderate to good yields from readily accessible and easy to handle starting materials under mild and metal-free conditions.
Zhu, Minghui,Wei, Wei,Yang, Daoshan,Cui, Huanhuan,Wang, Leilei,Meng, Guoqing,Wang, Hua
supporting information
p. 4789 - 4793
(2017/07/10)

Preparation method of sulfonamides compound
The invention discloses a reparation method of a sulfonamides compound. The preparation method includes: using thiophenol and amine which are simple and easy to get as raw materials; enabling the raw materials to be in direct oxidation coupling reaction under mediation of safe and stable iodine pentoxide to prepare sulfonamide. The preparation method has the advantages that reaction conditions are mild (60 DEG C), the raw materials are simple and easy to get and low in price, reaction environment is friendly, a substrate is wide in application range, and metal catalysts and harsh reaction conditions like low or high temperature and zero water and zero oxygen are not needed, so that metal pollution related to common synthesis methods is avoided; the preparation method further has the advantages of simple, convenient and safe operation, stable process condition and easiness in product purification and is suitable for large-scale production.
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Paragraph 0025; 0026

(2017/09/02)

Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates
Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.
Shyam, Pranab K.,Jang, Hye-Young
p. 1761 - 1767
(2017/02/10)

Copper-Catalyzed Sulfonylation of Alkenes and Amines by Using Thiosulfonates as a Sulfonylating Agent
Synthetically and pharmaceutically useful vinyl sulfones and sulfonamides are synthesized by the direct coupling of thiosulfonates with alkenes and amines, respectively. Copper catalysts help to generate the sulfonyl group from thiosulfonates and to form the C(sp2)–S/N–S bonds of the organosulfur compounds. This paper discusses the scope of these reactions of aromatic and aliphatic thiosulfonates with alkenes and amines.
Shyam, Pranab K.,Son, Soobin,Jang, Hye-Young
p. 5025 - 5031
(2017/09/22)

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 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.
p. 538 - 539
(2016/12/02)

One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides
Aryl ammonium sulfinates, conveniently prepared from aryl iodides and the sulfur dioxide surrogate DABSO, under the action of a palladium(0) catalyst, are transformed in a one-pot process to a variety of functionalized sulfonamides. The sulfinate to sulfonamide transformation is achieved by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino acid derivatives, are combined efficiently with a variety of aryl iodides, leading to sulfonamides in high yields.
Flegeau, Emmanuel Ferrer,Harrison, Jack M.,Willis, Michael C.
supporting information
p. 101 - 105
(2015/12/26)

Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
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
p. 590 - 597
(2016/01/12)

Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature
By using O-benzoyl hydroxylamines as amine sources, the first convenient copper-catalyzed electrophilic amination of sodium sulfinates has been realized. Even with 2 mol% catalyst loading, the protocol provided an efficient and straightforward synthesis of a broad range of functional sulfonamides under ambient reaction conditions without an additional base and ligand. Based on the control experiments, a plausible mechanism was proposed.
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Tu, Tao
supporting information
p. 16573 - 16576
(2015/11/18)

Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: A One-pot preparation of sulfonamides, amenable to array synthesis
We describe a method for the synthesis of sulfonamides through the combination of an organometallic reagent, a sulfur dioxide equivalent, and an aqueous solution of an amine under oxidative conditions (bleach). This simple reaction protocol avoids the need to employ sulfonyl chloride substrates, thus removing the limitation imposed by the commercial availability of these reagents. The resultant method allows access to new chemical space, and is also tolerant of the polar functional groups needed to impart favorable physiochemical properties required for medicinal chemistry and agrochemistry. The developed chemistry is employed in the synthesis of a targeted 70 compound array, prepared using automated methods. The array achieved a 93% success rate for compounds prepared. Calculated molecular weights, lipophilicities, and polar surface areas are presented, demonstrating the utility of the method for delivering sulfonamides with drug-like properties.
Deeming, Alex S.,Russell, Claire J.,Willis, Michael C.
p. 1168 - 1171
(2015/01/30)

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-mediated S-N formation via an oxygen-activated radical process: A new synthesis method for sulfonamides
Copper-mediated direct S-N formation using readily available starting materials via an oxygen-activated radical process has been developed. This method provides a novel and direct approach for synthesis of sulfonamides under air conditions. the Partner Organisations 2014.
Huang, Xin,Wang, Jichao,Ni, Zhangqin,Wang, Sichang,Pan, Yuanjiang
supporting information
p. 4582 - 4584
(2014/05/06)

N-CYCLIC SULFONAMIDO INHIBITORS OF GAMMA SECRETASE
The invention provides N-cyclic sulfonamido compounds for use in treating or preventing cognitive disorders, such as Alzheimer’s Disease. Compounds of particular interest are defined by Formula (I), wherein R4, R5, R6, Rs
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Page/Page column 54

(2010/02/14)

Steric and electronic effects on the partitioning of a persulfinyl intermediate along the physical quenching and chemical reaction channels
The rate constants, k(T), k(r), and k(Q), corresponding to the substrate induced total removal, chemical removal, and physical removal of singlet oxygen, respectively, have been measured for a series of sulfenamides. The structural effects on the partitioning of the persulfinamide intermediate along the chemical and physical deactivation pathways is discussed.
Clennan, Edward L.,Greer, Alexander
p. 6093 - 6096
(2007/10/03)

Photooxidation of sulfenic acid derivatives. 4.1,2 Reactions of singlet oxygen with sulfenamides
The reactions of singlet oxygen with nine sulfenamides are reported. A detailed kinetic study reveals that two intermediates are required on the photooxidation reaction surface. One intermediate acts as a nucleophile and the second intermediate as an electrophile in their reactions with diaryl sulfoxides and diaryl sulfides, respectively. Physical quenching is also suppressed in the sulfenamides relative to other sulfur-containing singlet oxygen substrates. The mechanism of the reaction is discussed and compared to diethyl sulfide photooxidation, and a rationale for the decreased importance of physical quenching in these substrates is presented.
Clennan, Edward L.,Zhang, Houwen
p. 4218 - 4227
(2007/10/02)