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Cinchona-alkaloid/Selectfluor combinations efficiently fluorinate a variety of carbonyl compounds in a highly enantioselective manner to furnish chiral alpha-fluorocarbonyl compounds. The DHQB/Selectfluor combination is effective for the enantioselective fluorination of indanones and tetralones 1 in up to 91% ee. The first enantioselective syntheses of chiral derivatizing reagents 3 was accomplished with high ee and in high chemical yields by the DHQDA/Selectfluor combination. 3-Fluorooxindoles 7 were prepared with ee up to 83% using the (DHQ)2AQN/Selectfluor or the (DHQD)2PYR/Selectfluor combination. Since the combinations are conveniently prepared in situ from readily available reagents, the present system represents a practical method for enantioselective fluorination. X-ray crystallography and 1H NMR analyses of the cinchona alkaloids/Selectfluor combination have established that the species that mediate this novel reaction are N-fluoroammonium cinchona alkaloid tetrafluoroborates, which adopt open conformations.

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Benzofuran – Wikipedia,
Benzofuran | C8H3505O – PubChem

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A fast and highly enantioselective fluorination of beta-keto esters catalyzed by diphenylamine linked bis(oxazoline)-Cu(OTf)2 complexes under solvent-free conditions has been developed using a planetary ball mill. High yields, high enantioselectivities and shorter reaction times were achieved with low catalyst loading.

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Benzofuran – Wikipedia,
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The first copper-catalyzed direct beta-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.

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Benzofuran – Wikipedia,
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This review presents a systematic and comprehensive survey of the utility of 4-hydroxy-2(1H)-quinolone as a building block of heterocyclic compounds. The reaction mechanism is considered as well as the scope and limitation of the most important of these approaches are demonstrated.

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Benzofuran – Wikipedia,
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In the present study we have made an attempt to synthesize novel benzofuran derivatives and evaluate them for anticancer screening. First, 2-carbethoxy-3 (2H) benzofuranone (2) was prepared by the condensation of ethyl bromomalonate with methyl salicylate (1) in presence of anhydrous potassium carbonate. Treatment of 2- carbethoxy-3 (2H) benzofuranone (2) with dimethylsulphate in presence of anhydrous potassium carbonate afforded 2-carbethoxy-3-methoxy benzofuranone (3). 2- Carbethoxy-3-methoxy benzofuranone (3) on treatment with hydrazine hydrate gave 3-methoxybenzofuran-2-carbohydrazide (4) and then condensation of 3- methoxybenzofuran-2-carbohydrazide (4) with various substituted benzaldehydes led to a novel series of benzofuran derivatives (5a-k). The synthesized compounds were analyzed by physical and analytical data. The synthesized compounds were evaluated for their short-term anticancer activity. The synthesized benzofuran derivative possessed significant cytotoxic activity against Ehrlich’s Ascites Carcinoma (EAC) cell lines and HEP2 cell line by Sulforhodamine B assay.

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Benzofuran – Wikipedia,
Benzofuran | C8H3503O – PubChem

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The selective construction of carbon-fluorine bonds is of great interest to medicinal chemists because the replacement of a hydrogen or an oxygen atom with a fluorine atom in biologically active molecules can confer the molecules with improved physicochemical properties and biological activities. Since the first discovery of enantioselective fluorination using N-fluorocamphorsultam, our synthetic interest had been focused on the development of chiral N-fluorosulfonamide derivatives capable of enantioselective fluorination. However, these initial efforts revealed several limitations in both chemical yields and enantioselectivities of the fluorinated products. We present here the background of our personal story of the enantioselective fluorination reaction and some successful applications of the methods to the design and synthesis of biologically active products. Two novel approaches using cinchona alkaloid/Selectfluor combinations and chiral ligands/metal complexes have been pursued, respectively. In addition, the recent advances in this area by other groups are also described briefly.

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Benzofuran – Wikipedia,
Benzofuran | C8H3504O – PubChem

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The synthesis of ethyl 3-hydroxybenzofuro<3,2-b>furan-2-carboxylate (3a), 2-acetyl-3-hydroxybenzofuro<3,2-b>furan (3b) and 3-hydroxybenzofuro<3,2-b>furan-2-carbonitrile (3c) from 2-carbethoxy-3(2H)-benzofuranone (1) by condensation with ethyl bromoacetate, chloracetone and chloroacetonitrile and subsequent Dieckmann cyclisation is reported.Reaction of 1 with aromatic amines under different reaction conditiones have also been investigated.

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3-Methoxybenzofuran-2-carbohydrazide (3), obtained from 2-carbethoxy-3-methoxybenzofuran (2), undergoes condensation isothiocyanates to furnish the corresponding thiosemicarbazides (4).Cyclisation of 4 in the presence of alkali furnishes the corresponding 2-(3′-mercapto-1′,2′,4′-triazol-5′-yl)-3-methoxybenzofurans (5).However, in presence of anhyd. orthophosphoric acid 4a-e yield 2-(5′-amino-1′,3′,4′-thiadiazol-2′-yl)-3-methoxybenzofurans (6a-e).Conversion of 3 into 3-methoxy-2-(1′,3′,4′-oxadiazol-2′-yl)-benzofuran (10) and its 5′-mercapto derivative (7) has also been carried out.

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Benzofuran – Wikipedia,
Benzofuran | C8H3492O – PubChem

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An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).

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Benzofuran – Wikipedia,
Benzofuran | C8H3514O – PubChem

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The study of the specific reactivity of the ion pairs of alkaline enolates of beta-dicarbonyl compounds shows that the lithium enolates, in spite of their characteristically strong enolate-cation interactions display, especially when compared to sodium enolates, a marked tendency towards O-alkylation.This strong O-/C-nucleophilicity of the lithium ion pairs is not very sensitive to changes in medium polarity (from THF or DME to DMF) but depends on the nature of the alkylating agent, being enhanced with moderately electrophilic alkyl sulfonates or sulfate but lessened with alkyl halides or with very electrophilic sulfonates (triflate).It is suggested that the litium enolate tendency towards O-alkylation is partly the result of a Li(+) – leaving group interaction (especially in the case of the sulfonates) and partly an intrinsic property of the enolate-lithium ion pair; this latter property is discussed in terms of the respective solvation abilities towards cations of the C- and O-alkylation transition states.Some of our results about the nucleophilic reactivity of ion pairs in DMF are at variance with previous reports in the literature.The origin of the discrepancy is discussed.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3502O – PubChem