Reactions of 1,3,5-tris(fluorosulfonyl)benzene with some nucleophilic reagents

Kamoshenkova, Oksana M.; Boiko, V. N.

doi:10.1016/j.jfluchem.2009.11.019

Cited by 13 publications

(6 citation statements)

References 29 publications

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“…The next object of our investigation, 1,3,5-tris (b,b,b-trifluoroethoxysulfonyl)benzene 3 was obtained in our laboratory during the course of investigation of the sulfonyl center reactivity in compound 2 [12]. It should be noted that SO 2 OCH 2 CF 3 group is a rather electron withdrawing substituent (s p -SO 2 OCH 2 CF 3 = 0.88 [11]).…”

Section: Resultsmentioning

confidence: 99%

Stable gem-trifluoromethyl anionic σ-complexes based on 1,3,5-tris(sulfonyl)benzene derivatives and their transformations

Holovko-Kamoshenkova

Kirij

Boiko

et al. 2010

Journal of Fluorine Chemistry

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Section: Resultsmentioning

confidence: 99%

Stable gem-trifluoromethyl anionic σ-complexes based on 1,3,5-tris(sulfonyl)benzene derivatives and their transformations

Holovko-Kamoshenkova

Kirij

Boiko

et al. 2010

Journal of Fluorine Chemistry

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“…26 Taunton and coworkers designed inhibitors 23 and 24 based on the structure and reactivity of ATP mimic p -fluorosulfonylbenzoyl 5'-adenosine (FSBA, 22 ), a compound that covalently binds to all nine Src kinases via a mechanism involving the addition of Lys295 to the fluorosulfonyl group and fluoride elimination (Figure 6). 26-27 This work showed that substituting a vinylsulfone for the fluorosulfonyl group led to a covalent bond between 23 and three of the Src kinases, only those containing the conserved cysteine (Cys277). Additionally, vinylsulfone 23 was 40-fold less potent than fluorosulfonyl benzoate 24 against off-target kinases lacking this G-loop cysteine.…”

Section: Introductionmentioning

confidence: 99%

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

et al. 2016

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Although Michael acceptors display a potent and broad spectrum of bioactivity, they have largely been ignored in drug discovery because of their presumed indiscriminate reactivity. As such, a dearth of information exists relevant to the thiol reactivity of natural products and their analogs possessing this moiety. In the midst of recently approved acrylamide-containing drugs, it is clear that a good understanding of the hetero-Michael addition reaction and the relative reactivities of biological thiols with Michael acceptors under physiological conditions is needed for the design and use of these compounds as biological tools and potential therapeutics. This perspective provides information that will contribute to this understanding, such as kinetics of thiol addition reactions, bioactivities, as well as steric and electronic factors that influence the electrophilicity and reversibility of Michael acceptors. This perspective is focused on α,β-unsaturated carbonyls given their preponderance in bioactive natural products.

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“…Sulfonamidations with simple aliphatic and aromatic amines have met with limited success until recently [16] . Most reactions with reasonable yields involved the use of activated substrates [16c,h] . Very recently, am Ende and Ball developed an elegant system for the activation of sulfur(VI) fluorides.…”

Section: Introductionmentioning

confidence: 99%

A Broad‐Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

et al. 2021

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A broad‐spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1‐hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram‐scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.

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Reactions of 1,3,5-tris(fluorosulfonyl)benzene with some nucleophilic reagents

Cited by 13 publications

References 29 publications

Stable gem-trifluoromethyl anionic σ-complexes based on 1,3,5-tris(sulfonyl)benzene derivatives and their transformations

Stable gem-trifluoromethyl anionic σ-complexes based on 1,3,5-tris(sulfonyl)benzene derivatives and their transformations

Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions

A Broad‐Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

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