Silver-catalyzed vinylic C-F bond activation : synthesis of 2-fluoroindoles from β,β-difluoro-o-sulfonamidostyrenes
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DOI[10.1246/cl.160427]to the data of the same series
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- Material Type
- 記事
- Author/Editor
- Takeshi FujitaYota WatabeShigeyuki Yamashita
- Publication, Distribution, etc.
- Publication Date
- 2016-05-20
- Publication Date (W3CDTF)
- 2016-05-20
- Periodical title
- Chemistry letters
- No. or year of volume/issue
- 45(8)
- Volume
- 45(8)
- ISSN (Periodical Title)
- 1348-0715
- ISSN-L (Periodical Title)
- 0366-7022
- Text Language Code
- eng
- DOI
- 10.1246/cl.160427
- Persistent ID (NDL)
- info:ndljp/pid/11459678
- Collection
- Collection (Materials For Handicapped People:1)
- Collection (particular)
- 国立国会図書館デジタルコレクション > 電子書籍・電子雑誌 > 学術機関 > 学協会
- Acquisition Basis
- オンライン資料収集制度
- Date Accepted (W3CDTF)
- 2020-03-13T20:40:24+09:00
- Date Captured (W3CDTF)
- 2020-03-13
- Format (IMT)
- application/pdf
- Access Restrictions
- 国立国会図書館内限定公開
- Service for the Digitized Contents Transmission Service
- 図書館・個人送信対象外
- Availability of remote photoduplication service
- 可
- Periodical Title (URI)
- Periodical Title (Persistent ID (NDL))
- info:ndljp/pid/11459665
- Data Provider (Database)
- 国立国会図書館 : 国立国会図書館デジタルコレクション
- Summary, etc.
- An electrophilic 5-<i>endo</i>-<i>trig</i> cyclization of β,β-difluoro-<i>o</i>-sulfonamidostyrenes was performed in 1,1,1,3,3,3-hexafluoropropan-2-ol using a Ag(I) catalyst and <i>N</i>,<i>O</i>-bis(trimethylsilyl)acetamide. In this process, vinylic C–F bond activation was achieved via silver-catalyzed β-fluorine elimination, accompanied by C–N bond formation, which led to the synthesis of 2-fluoroindoles.
- DOI
- 10.1246/cl.160427
- Access Restrictions
- インターネット公開
- Data Provider (Database)
- 科学技術振興機構 : J-STAGE
- Summary, etc.
- An electrophilic 5-<i>endo</i>-<i>trig</i> cyclization of β,β-difluoro-<i>o</i>-sulfonamidostyrenes was performed in 1,1,1,3,3,3-hexafluoropropan-2-ol using a Ag(I) catalyst and <i>N</i>,<i>O</i>-bis(trimethylsilyl)acetamide. In this process, vinylic C–F bond activation was achieved via silver-catalyzed β-fluorine elimination, accompanied by C–N bond formation, which led to the synthesis of 2-fluoroindoles.
- DOI
- 10.1246/cl.160427
- Related Material (URI)
- Is Referenced By
- Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Brønsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3‐Hexafluoropropan‐2‐olAluminium-mediated aromatic C-F bond activation: regioswitchable construction of benzene-fused triphenylene frameworksConstruction of Pinpoint-Fluorinated Benzothiophene Frameworks Using Palladium-Catalyzed Cyclization of o-(Fluorovinyl)phenyl-Substituted ThiophenesRing-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenesNucleophilic 5-endo-trig cyclization of 2-(trifluoromethyl)allylic metal enolates and enamides: Synthesis of tetrahydrofurans and pyrrolidines bearing exo-difluoromethylene unitsNickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activationHighly Active Cross-Metathesis of Tetrafluoroethylene with a Seven-Membered N-Heterocyclic-Carbene–Ruthenium CatalystSynthesis of 3‐CF<sub>3</sub>‐Indoles from HFO‐1234ze(<i>E</i>) via Cross‐Coupling and Intramolecular CyclizationSynthesis of 3‐(Trifluoromethyl)indoles by Oxidative Cyclization of <i>o</i>‐Sulfonamido‐α‐(trifluoromethyl)styrenesTransition‐Metal‐Mediated and ‐Catalyzed C−F Bond Activation by Fluorine EliminationLewis Acid-mediated Carbon-Fluorine Bond Transformation: Substitution of Fluorine and Insertion into a Carbon-Fluorine Bond遷移金属によるフッ素脱離過程を利用したアリル位およびビニル位炭素-フッ素結合活性化
- References
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<i>via</i> Nickel‐ Catalyzed Kumada‐Type Cross‐Coupling Reaction of <i>gem</i>‐ Difluoroalkenes with Di‐Grignard ReagentsEfficient Helicene Synthesis: Friedel–Crafts‐type Cyclization of 1,1‐Difluoro‐1‐alkenesCF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl‐3,5‐diaryl‐2‐oxazolidinones by Desymmetrization of 2‐Aryl‐1,3‐difluoropropan‐2‐olsMethod for the Synthesis of Dibenzo[<i>g</i>,<i>p</i>]Chrysenes: Domino Friedel–Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl GroupsA Synthesis of Dihydrofuran-3(2<i>H</i>)-ones5-Endo-trigonal reactions: a disfavoured ring closurePd-catalyzed 5-<i>endo-trig</i>-type cyclization of β,γ-unsaturated carbonyl compounds: an efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-onesRhodium-catalysed C(sp2)–C(sp2) bond formation via C–H/C–F activationCopper-Catalyzed <i>gem</i>-Difluoroolefination of Diazo Compounds with TMSCF<sub>3</sub> via C–F Bond CleavageSynthesis of <i>gem</i>-Difluoroalkenes via β-Fluoride Elimination of Organorhodium(I)Double CF Bond Activation through β‐Fluorine Elimination: Nickel‐Mediated [3+2] Cycloaddition of 2‐Trifluoromethyl‐1‐alkenes with AlkynesPinpoint-fluorinated phenanthrene synthesis based on C F bond activation of difluoroalkenesNucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated DihydroheterolesActivation of 1,1-Difluoro-1-alkenes with a Transition-Metal Complex: Palladium(II)-Catalyzed Friedel–Crafts-Type Cyclization of 4,4-(Difluorohomoallyl)arenesLewis Acid‐Catalyzed or Base‐Promoted Regioselective Cycloisomerization of <i>N</i>‐Imidoyl‐<i>o</i>‐alkynylanilines for Synthesis of <i>N</i>‐Imidoyl‐(1 <i>H</i>)‐indoles and 4‐Alkylidene‐3,4‐dihydroquinazolinesNickel-Catalyzed Allylic C(sp<sup>3</sup>)–F Bond Activation of Trifluoromethyl Groups via β-Fluorine Elimination: Synthesis of Difluoro-1,4-dienesPinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement StrategiesPalladium- and Nickel-Catalyzed Kumada Cross-Coupling Reactions of <i>gem</i>-Difluoroalkenes and Monofluoroalkenes with Grignard ReagentsDiastereoselective Intramolecular Allyl Transfer from Allyl Carbamate Accompanied by 5‐<i>endo</i>‐trig Ring ClosureFriedel-Crafts Cyclization of 1,1-Difluoroalk-1-enes: Synthesis of Benzene-Fused Cyclic Ketones via α-FluorocarbocationsCu(I)-Catalyzed Cross-Coupling of Terminal Alkynes with Trifluoromethyl Ketone <i>N</i>-Tosylhydrazones: Access to 1,1-Difluoro-1,3-enynesRing constructions by the use of fluorine substituent as activator and controllerFunctionalization of Fluorinated Molecules by Transition-Metal-Mediated C–F Bond Activation To Access Fluorinated Building BlocksFluorinated Alcohols: A New Medium for Selective and Clean ReactionA Robust, Well‐Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2‐Ethynylanilines Leading to IndolesFluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous CatalysisRules for ring closureC−F Bond Activation in Organic SynthesisVinylic CF bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconoceneFluorine-Directed Nazarov Cyclizations: A Controlled Synthesis of Cross-Conjugated 2-Cyclopenten-1-onesReactions of 1,1-difluoro-1-olefins with electrophilic reagents5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes: synthesis of 4-difluoromethylene-substituted 1-pyrrolinesFluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) saltsSignificant Enhancement in the Efficiency and Selectivity of Iron‐Catalyzed Oxidative Cross‐Coupling of Phenols by FluoroalcoholsSynthesis of fluorostyrenes via palladium‐catalyzed reactions of aromatic halides with fluoroolefinsCarbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amineAn improved cyclisation protocol for the synthesis of δ,δ-difluoro-δ-lactones.A Surprising Substituent Effect Provides a Superior Boronic Acid Catalyst for Mild and Metal‐Free Direct Friedel–Crafts Alkylations and Prenylations of Neutral ArenesFriedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen BondingFluorinated alcohols: A magic medium for the synthesis of heterocyclic compoundsThe Nucleophilic 5<i>-endo-trig</i> Cyclization of 1,1<i>-</i>Difluoro-1-alkenes: Ring-Fluorinated Hetero- and Carbocycle Synthesis and Remarkable Effect of the Vinylic Fluorines on the Disfavored ProcessIntramolecular 5-<i>endo</i>-trig aminopalladation of β-hydroxy-γ-alkenylamine: efficient route to a pyrrolidine ring and its application for the synthesis of (−)-8,8a-di-<i>epi</i>-swainsonineFriedel−Crafts-Type Cyclization of 2,2-Difluorovinyl Ketones via α-Fluorocarbocations and Its Application in Domino CyclizationsTotal synthesis of natural cis-3-hydroxy-l-proline from d-glucoseIntramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanolPd‐Catalyzed Regioselective Activation of <i>gem</i>‐Difluorinated Cyclopropanes: A Highly Efficient Approach to 2‐Fluorinated Allylic ScaffoldsElectrophilic cyclization reaction of gem-difluoroolefin derivatives: Syntheses of 6,6-difluorotetrahydro-2-pyrones and 2,2-difluorotetrahydropyran via halogen induced cyclization.Transition-metal-catalyzed Electrophilic Activation of 1,1-Difluoro-1-alkenes: Oxindole Synthesis via Intramolecular AminationCopper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate
- Data Provider (Database)
- 国立情報学研究所 : CiNii Research
- Original Data Provider (Database)
- Japan Link Center雑誌記事索引データベースCrossrefCiNii Articles科学研究費助成事業データベース科学研究費助成事業データベース科学研究費助成事業データベース科学研究費助成事業データベースCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossref
- Bibliographic ID (NDL)
- 11459678
- NAID
- 130005254491