Aryl Fluorosulfate Trapped Staudinger Reduction

Ren, Gerui; Zheng, Qinheng; Wang, Hua

doi:10.1021/acs.orglett.7b00406

Cited by 22 publications

(14 citation statements)

References 19 publications

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“…Considering the monocovalent attachment mode of 1, with the second -SO 2 F intact, it was envisaged that 1 of the 2 sulfonyl fluoride groups could be substituted so as to perhaps improve the capture rate, and/or selective binding (Table 1). A set of benzenesulfonyl fluoride cores carrying ortho-substituents (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24) was therefore examined. Compounds 8-18 (90) were synthesized by the efficient aqueous potassium bifluoride exchange procedure from commercially available sulfonyl chlorides but showed poorer reactivity/binding with hNE.…”

Section: Resultsmentioning

confidence: 99%

“…click chemistry | SuFEx | agnostic | covalent inhibitor | elastase S ulfur fluoride exchange (SuFEx)-the new-generation click chemistry, since first introduced in 2014 (1), has quickly found diverse applications across an array of fields (DOI: 10.1039/C8CS00960K), including chemical synthesis (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), material science (13)(14)(15)(16)(17)(18)(19), chemical biology (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32), and drug discovery (33,34). SuFEx creates robust intermolecular links between modules.…”

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confidence: 99%

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SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Zheng

Woehl

Kitamura

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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133

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Sulfur fluoride exchange (SuFEx) has emerged as the new generation of click chemistry. We report here a SuFEx-enabled, agnostic approach for the discovery and optimization of covalent inhibitors of human neutrophil elastase (hNE). Evaluation of our ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride. Synthetic derivatization of the initial hit led to a more potent agent, 2-(fluorosulfonyl)phenyl fluorosulfate with IC50 0.24 μM and greater than 833-fold selectivity over the homologous neutrophil serine protease, cathepsin G. The optimized, yet simple benzenoid probe only modified active hNE and not its denatured form.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Zheng

Woehl

Kitamura

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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140

133

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“…Consequently, they are often considered as efficient triflate surrogates, albeit at a much lower production cost. Furthermore, aryl fluorosulfates are also versatile intermediates as they can be converted into aryl fluorides, aryl sulfamate esters, and others or can even be used for the synthesis of anhydrous tetraalkylammonium fluoride salts …”

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confidence: 99%

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

et al. 2017

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A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SOF). The proposed method employs 1,1'-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SOF 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.

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“…Wang and co‐workers developed an interesting chemoselective Staudinger reduction/SuFEx cascade reaction to join two chemical segments together through an aryl sulfamate ester (RNH−SO 2 −OAr) linkage (Scheme ) . 2‐(Diphenylphosphanyl) phenyl fluorosulfate ( 114 ) reacted with azide derivatives in [D 6 ]DMSO that contained 5 % water at 37 °C to give aryl sulfamate esters 115 in excellent yields.…”

Section: Chemical Transformationsmentioning

confidence: 99%

Synthesis and Chemical Transformations of Fluorosulfates

Lekkala

Leng

et al. 2018

Asian J Org Chem

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Fluorosulfates are readilya vailablee lectrophiles that can be prepared from the reactions of phenol or alcohol derivatives with sulfuryl fluoride, fluorosulfonic acid, sulfuryl chloridef luoride, and fluorosulfonic anhydride. This Focus Review coversm ost of the synthetic strategies that have been reported for the construction of fluorosulfates,a s well as their application as versatile buildingb locks in av ariety of synthetic transformations, such as catalyzed amination, cross-coupling, sulfur(VI) fluoridee xchange, carbonylation, hydrolysis, alcoholysis,a nd as alternatives to organic halidesort riflates in organic chemistry.Scheme79. Synthesis of g-pyrone by using fluorosulfate 34.Scheme80. Reactions of fluorosulfatesw ith nucleophilicreagents.Scheme81. Synthesis of the desired allenefrom fluorosulfate 68. Scheme82. Preparation of benzenef rom phenyl fluorosulfate (110).Scheme83. Synthesis of compound 170 from fluorosulfate 169.

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Aryl Fluorosulfate Trapped Staudinger Reduction

Cited by 22 publications

References 19 publications

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

Synthesis and Chemical Transformations of Fluorosulfates

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