Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of <i>gem</i>-Difluoroalkenes

Orsi, Douglas L.; Douglas, Justin T.; Sorrentino, Jacob P.; Altman, Ryan A.

doi:10.1021/acs.joc.0c00415

Cited by 18 publications

(14 citation statements)

References 87 publications

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“…4ab, entry 2). [33] Further, use of CuCl instead of CuCl2 lowered the conversion of substrates and delivered lower yield of ketone (entry 3). Replacement of terpyridine with bipyridine or phenanthroline provided lower yield of the desired product (entries 4 and 5).…”

Section: Resultsmentioning

confidence: 99%

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

et al. 2022

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“…This regioselective attack of the radical to the difluorinated position is consistent with other radical functionalization reactions of alkenes. [27,28,33,[43][44][45] Trapping of radical 11 with Cu I Cl and molecular oxygen affords peroxo intermediate 12. Concerted elimination of Cu II oxide 12 might afford product 3 and Cu I Cl(OH) 13, [40,41,46,47] which could react with HCl to regenerate the active catalyst Cu II Cl2.…”

Section: Resultsmentioning

confidence: 99%

Cu(II) Catalyzed Unsymmetrical Di-oxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-Phenoxyketones, an Unstudied Substructure

Koley

Cayton

González‐Montiel

et al. 2021

Preprint

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A Cu-based catalyst system convergently couples gem-difluoroalkenes with phenols under aerobic conditions to deliver α,α-difluorinated-α-phenoxy ketones, an unstudied hybrid fluorinated functional group. Composed of α,α-difluorinated ketone and α,α-difluorinated ether moieties, these have only once been previously reported as a synthetic intermediate en route to pharmacologically active compounds. Computational predictions and later experimental corroboration suggest that the sp3-hybridized hydrate adduct of the phenoxy-substituted fluorinated ketone is energetically accessible. The more facile conversion between ketone and hydrate forms suggest that covalent inhibition of proteases and other enzymes may be possible. Further functionalization of the ketone group enables access to other useful fluorinated functional groups.

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“…In this study, 12 N-phenylsulfonamide derivatives (1-12) as the target molecules were obtained in one step in good to excellent yields according to the previously reported method. 57 These inhibitors were acquired with 79-85% yields by reactions of four substituted benzenesulfonyl chlorides with 2-, 3-, and 4-aminophenol in the presence of pyridine in dichloromethane (DCM). The synthetic pathway for their synthesis was presented in Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

Biological activity and molecular docking studies of some N‐phenylsulfonamides against cholinesterases and carbonic anhydrase isoenzymes

Başaran

Çakmak

Şentürk

et al. 2022

J of Molecular Recognition

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In this research, a series of N‐phenylsulfonamide derivatives (1‐12) were designed, synthesized, and investigated for their inhibitory potencies against carbonic anhydrase isoenzymes I, II, and IX (hCA I, hCA II, and hCA IX) and cholinesterases (ChE), namely, acetylcholinesterase and butyrylcholinesterase. These compounds, whose inhibition potentials were evaluated for the first time, were characterized by spectroscopic techniques (1H‐ and 13C‐NMR and FT‐IR). CA isoenzyme inhibitors are significant therapeutic targets, especially owing to their preventive/activation potential in the therapy processes of some diseases such as cancer, osteoporosis, and glaucoma. On the other hand, Cholinesterase inhibitors are valuable molecules with biological importance that can be employed in the therapy process of Alzheimer's patients. The results showed that the tested molecules had enzyme inhibition activities ranging from 9.7 to 93.7 nM against these five metabolic enzymes. Among the tested molecules, the methoxy and the hydroxyl group‐containing compounds 10, 11, and 12 exhibited more enzyme inhibition activities when compared to standard compounds acetazolamide, sulfapyridine, and sulfadiazine for CA isoenzymes and neostigmine for ChE, respectively. Of these three molecules, compound 12, which had a hydroxyl group in the para position in the aromatic ring, was determined to be the most active molecule against all enzymes. In silico work, molecular docking has also shown similar results and is consistent with the experimental data in the study. As a result, we can say that some of the tested molecules might be used as promising inhibitor candidates for further studies on this topic.

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Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of gem-Difluoroalkenes

Cited by 18 publications

References 87 publications

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

Cu(II) Catalyzed Unsymmetrical Di-oxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-Phenoxyketones, an Unstudied Substructure

Biological activity and molecular docking studies of some N‐phenylsulfonamides against cholinesterases and carbonic anhydrase isoenzymes

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