51451-34-4Relevant academic research and scientific papers
Ex situ generation of sulfuryl fluoride for the synthesis of aryl fluorosulfates
Veryser, Cedrick,Demaerel, Joachim,Bieliunas, Vidmantas,Gilles, Philippe,De Borggraeve, Wim M.
, p. 5244 - 5247 (2017)
A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SO2F2). The proposed method employs 1,1'-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SO2F2 gas using a two-chamber reactor. With NMR studies, it was shown that this ex situ gas evolution is extremely rapid, and a variety of phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.
Deoxyfluorination of alcohols with aryl fluorosulfonates
Fei, Zhongbo,Hu, Jinbo,Li, Wei,Liu, Qinghe,Ni, Chuanfa,Wang, Xiu,Zhou, Min
supporting information, p. 8170 - 8173 (2021/08/23)
Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.
A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction
Ferraro, Samantha L.,Flynn, James P.,Hwang, Seung,Liu, Chao,Niu, Jia,Yang, Cangjie
supporting information, p. 18435 - 18441 (2020/08/25)
O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.
A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls
Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting
supporting information, p. 4748 - 4753 (2020/08/17)
A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.
Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies
Ravindar, Lekkala,Bukhari,Rakesh,Manukumar,Vivek,Mallesha,Xie, Zhi-Zhong,Qin, Hua-Li
, p. 107 - 118 (2018/08/21)
A series of aryl fluorosulfate analogues (1–37) were synthesized and tested for in vitro antibacterial and antifungal studies, and validated by docking studies. The compounds 9, 12, 14, 19, 25, 26, 35, 36 and 37 exhibited superior antibacterial potency ag
Sulfur(VI) fluoride compounds and methods for the preparation thereof
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Page/Page column 19; 20; 38; 40; 56; 57, (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.
Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates
Schimler, Sydonie D.,Cismesia, Megan A.,Hanley, Patrick S.,Froese, Robert D.J.,Jansma, Matthew J.,Bland, Douglas C.,Sanford, Melanie S.
supporting information, p. 1452 - 1455 (2017/02/10)
This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.
Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates
Liang, Qiaobin,Xing, Ping,Huang, Zuogang,Dong, Jiajia,Sharpless, K. Barry,Li, Xiaoxian,Jiang, Biao
supporting information, p. 1942 - 1945 (2015/04/27)
Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and proceeded smoothly to give excellent yields. Aryl fluorosulfates could also be used as alternatives to halides or triflates in other coupling reactions.
Palladium Cross-Coupling Reactions of Aryl Fluorosulfonates: An Alternative to Triflate Chemistry
Roth, Gregory P.,Fuller, Carl E.
, p. 3493 - 3496 (2007/10/02)
A new and efficient electrophilic partner for palladium(0)-catalyzed cross coupling is reported.Aryl fluorosulfonates are readily prepared in high yield by treatment of the appropriate phenol with fluorosulfonate anhydride.The palladium-catalyzed coupling reactions of these fluorosulfonates with vinyl- and aryltin reagents, as well as organozinc chlorides, takes place under mild conditions in a regio- and stereoselective manner.
