329-98-6Relevant articles and documents
Method for preparing alkyl sulfonyl fluoride
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Paragraph 0084-0087, (2021/11/27)
The invention relates to a method for preparing alkyl sulfonyl fluoride, wherein the reducing active ester converted from alkyl carboxylic acid is a raw material, the sulfur dioxide substitution reagent is a sulfur dioxide source, and the electrophilic fluorinating reagent is a fluorine source. Compared with the prior art, the synthesis method is simple, has the selectivity of in-situ introduction of the sulfonyl fluoride group and high yield, and is easy to implement large-scale production.
Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information, p. 8488 - 8493 (2021/11/01)
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
Method for efficiently preparing sulfuryl fluorides compound by catalytic fluorination
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Paragraph 0075; 0076; 0077; 0078, (2019/05/22)
The invention belongs to the technical field of the chemical synthesis, and particularly relates to a method for efficiently preparing a sulfuryl fluorides compound by catalytic fluorination. The provided method for efficiently preparing the sulfuryl fluorides compound by the catalytic fluorination comprises the following steps: enabling a sulfonyl chlorides compound to react with a hydroge fluoride under the action of a catalyst of a sulfonic acids derivative, to obtain the sulfuryl fluorides compound. A novel catalytic technology is provided, and the method has extensive substrate applicability. Efficient catalytic efficiency and yield are expressed.
Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
Laudadio, Gabriele,Bartolomeu, Aloisio De A.,Verwijlen, Lucas M. H. M.,Cao, Yiran,De Oliveira, Kleber T.,No?l, Timothy
supporting information, p. 11832 - 11836 (2019/08/26)
Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.
Sulfur(VI) fluoride compounds and methods for the preparation thereof
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Page/Page column 19; 20; 36; 45; 47, (2018/11/23)
This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.
Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
, p. 2244 - 2247 (2017/05/16)
A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
A fluoride compound of preparation method
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Paragraph 0100; 0101; 0102, (2017/08/25)
The invention relates to a preparation method of a sulfuryl fluoride compound. A sulfonyl hydrazide compound and a fluoride reagent serve as reaction raw materials. The preparation method includes the steps that a, the sulfonyl hydrazide compound with the structure (I) and the fluoride reagent are dispersed in a solvent, wherein the structure (I) is shown in the specification; b; a mixture obtained from the step a is stirred and heated to obtain the sulfuryl fluoride compound with the structure (II), wherein the structure (II) is shown in the specification (II). Compared with existing related technologies in the chemical synthesis field, the method of preparing sulfuryl fluoride from sulfonyl hydrazide is achieved for the first time. In the method, no catalyst needs to be added, reaction conditions are moderate, good compatibility can be achieved for water and air, and large-scale production is easy to achieve. The experimental result indicates that the yield of the obtained sulfuryl fluoride compound can reach up to 98%.
One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
Davies, Alyn T.,Curto, John M.,Bagley, Scott W.,Willis, Michael C.
, p. 1233 - 1237 (2017/02/10)
A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.
Catalyst-free radical fluorination of sulfonyl hydrazides in water
Tang, Lin,Yang,Wen, Lixian,Yang, Xingkun,Wang, Zhiyong
, p. 1224 - 1228 (2016/03/09)
The first catalyst-free fluorination of sulfonyl hydrazides for the synthesis of sulfonyl fluorides has been developed via a free-radical pathway. This protocol presents a broad substrate scope and does not require any metal catalyst and additive. All these transformations proceed smoothly in water under mild conditions, which enables a straightforward, practical and environmentally benign fluorination for S-F bond formation.
Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
Kirihara, Masayuki,Naito, Sayuri,Nishimura, Yuki,Ishizuka, Yuki,Iwai, Toshiaki,Takeuchi, Haruka,Ogata, Tomomi,Hanai, Honoka,Kinoshita, Yukari,Kishida, Mari,Yamazaki, Kento,Noguchi, Takuya,Yamashoji, Shiro
, p. 2464 - 2471 (2014/04/03)
The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.
