Development of shelf-stable reagents for fluoro-functionalization reactions
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- Material Type
- 記事
- Author/Editor
- Norio Shibata
- Publication, Distribution, etc.
- Publication Date
- 2016-08-05
- Publication Date (W3CDTF)
- 2016-08-05
- Periodical title
- Bulletin of the Chemical Society of Japan
- No. or year of volume/issue
- 89(11)
- Volume
- 89(11)
- ISSN (Periodical Title)
- 1348-0634
- ISSN-L (Periodical Title)
- 0009-2673
- Text Language Code
- eng
- DOI
- 10.1246/bcsj.20160223
- Persistent ID (NDL)
- info:ndljp/pid/11343269
- 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)
- 2019-08-27T20:45:33+09:00
- Date Captured (W3CDTF)
- 2019-08-27
- 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/11343267
- 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
- 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
- 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
- Holding library
- 国立国会図書館
- Call No.
- Z53-B35
- Related Material (URI)
- Related Material (Persistent ID (NDL))
- info:ndljp/pid/11343269
- Data Provider (Database)
- 国立国会図書館 : 国立国会図書館雑誌記事索引
- Bibliographic ID (NDL)
- 027719275
- Bibliographic Record Category (NDL)
- 632
- Summary, etc.
- <p>It is highly probable that the first impression that organic chemists would have of fluorine, <b>F</b>, is that it is “dangerous”. Elemental fluorine, F<sub>2</sub>, is a gas that reacts with all elements quickly and violently. The oxidation power of F<sub>2</sub> is extraordinarily strong and even the noble gases such as Kr and Xe react with F<sub>2</sub> forming the corresponding fluorides. Fortunately, the receptiveness to fluorine chemistry by synthetic chemists has gradually changed in the late 20th century with the development of shelf-stable reagents for fluorination and trifluoromethylation reactions. In this account, I introduce our recent contributions to the development of shelf-stable reagents for the synthesis of organofluorine compounds. Electrophilic reagents for fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation are discussed. Nucleophilic reagents for monofluoromethylation are also described including enantioselective reactions.</p>
- DOI
- 10.1246/bcsj.20160223
- 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.
- <p>It is highly probable that the first impression that organic chemists would have of fluorine, <b>F</b>, is that it is “dangerous”. Elemental fluorine, F<sub>2</sub>, is a gas that reacts with all elements quickly and violently. The oxidation power of F<sub>2</sub> is extraordinarily strong and even the noble gases such as Kr and Xe react with F<sub>2</sub> forming the corresponding fluorides. Fortunately, the receptiveness to fluorine chemistry by synthetic chemists has gradually changed in the late 20th century with the development of shelf-stable reagents for fluorination and trifluoromethylation reactions. In this account, I introduce our recent contributions to the development of shelf-stable reagents for the synthesis of organofluorine compounds. Electrophilic reagents for fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation are discussed. Nucleophilic reagents for monofluoromethylation are also described including enantioselective reactions.</p>
- DOI
- 10.1246/bcsj.20160223
- Access Restrictions
- インターネット公開
- Related Material (URI)
- Is Referenced By
- C−F Arylation of Polyfluorophenols by Means of Sigmatropic Dearomatization/Defluorination SequenceRegioselective Difunctionalization of 2,6-Difluorophenols Triggered by Sigmatropic DearomatizationModern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical NeedsSynthesis of α-Fluoroimines by Copper-catalyzed Reaction of Diarylacetylenes and <i>N</i>-FluorobenzenesulfonimideAnionic Triflyldiazomethane: Generation and Its Application for Synthesis of Pyrazole-3-triflones via [3 + 2] Cycloaddition ReactionSigmatropic Dearomatization/Defluorination Strategy for C−F Transformation: Synthesis of Fluorinated Benzofurans from PolyfluorophenolsKitamura Electrophilic Fluorination Using HF as a Source of FluorineOne-step Synthesis of 2-Hydroxy-2-(trifluoromethyl)malonates by Trifluoromethylation of 2-Oxomalonates with Ruppert-Prakash ReagentPerfluoroalkyl Analogues of Diethylaminosulfur Trifluoride: Reagents for Perfluoroalkylthiolation of Active Methylene Compounds under Mild ConditionsCurrent Contributions of Organofluorine Compounds to the Agrochemical IndustryDeoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD<sup>®</sup>/Olah’s reagent under solvent-free conditionsTransition Metal‐Catalyzed Cross‐Couplings of Benzylic Sulfone DerivativesSolid surface vs. liquid surface: nanoarchitectonics, molecular machines, and DNA origamiModular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling<i>N</i>‐Fluoro Ammonium Salts of <i>Cinchona</i> Alkaloids in Enantioselective Electrophilic FluorinationCurrent State of Microflow Trifluoromethylation ReactionsDynamism of supramolecular DNA/RNA nanoarchitectonics: From interlocked structures to molecular machines
- References
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Thiolation—Mild and Efficient Synthesis of Trifluoromethyl ThioethersN,N-Dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate: A versatile electrophilic difluoromethylating reagentDirect Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra‐<i>n</i>‐butylammonium IodideInherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl EthersThree‐component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of CC Bonds Mediated by Photoredox CatalystsPhotoredox‐Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated AlkenesEfficient Difluoromethylation of sp<sup>3</sup> Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic BasesChiral <i>N</i>‐Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative FluorinationAsymmetric Synthesis of Both Mirror Images of 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XXVI. Preparation and synthetic applications of (dimethylamino)phenyloxosulfonium methylide2‐Fluoro‐1,3‐benzodithiole‐1,1,3,3‐tetraoxide: A Reagent for Nucleophilic Monofluoromethylation of AldehydesPd‐Catalyzed Synthesis of ArSCF<sub>3</sub> Compounds under Mild ConditionsCopper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Desulfonylation and C(sp<sup>2</sup>)–N Bond Formation of Conjugated Tosyl AmidesThalidomideHighly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-KetoestersCinchona Alkaloid-Catalyzed Enantioselective Monofluoromethylation Reaction Based on Fluorobis(phenylsulfonyl)methane Chemistry Combined with a Mannich-type ReactionSynthesis and Properties of Bis-(trifluoromethylthio)-mercuryLewis Acid Mediated Trifluoromethylthio Lactonization/LactamizationCopper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C–H Bond ActivationBildung von C‐SCF<sub>3</sub>‐Bindungen durch direkte TrifluormethylthiolierungMild copper-catalyzed trifluoromethylation of terminal alkynes using an electrophilic trifluoromethylating reagentThe Polar Fluorination of PropenylbenzeneCopper-mediated trifluoromethylation of propiolic acids: facile synthesis of α-trifluoromethyl ketonesDirect Trifluoromethylthiolation of Unactivated C(sp<sup>3</sup>)H Using Silver(I) Trifluoromethanethiolate and Potassium PersulfateCopper‐Catalyzed Trifluoromethylation of Unactivated OlefinsSynthese und oxidation von 7-trifluormethylthiocycloheptatrien<i>N</i>‐Trifluormethylthiophthalimid: ein stabiles, elektrophiles SCF<sub>3</sub>‐ Reagens und seine Anwendung in der katalytischen asymmetrischen TrifluormethylsulfenylierungTrifluoromethanesulfanylamides as Easy‐to‐Handle Equivalents of the Trifluoromethanesulfanyl Cation (CF<sub>3</sub>S<sup>+</sup>): Reaction with Alkenes and AlkynesAryl Fluoroalkyl Sulfides. II. 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X. 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S-, Se-, and Te-(trifluoromethyl)dibenzothio-, -seleno-, and -tellurophenium salt systemMild and Soft Catalyzed Trifluoromethylthiolation of Boronic Acids: The Crucial Role of WaterElectrophilic Trifluoromethanesulfanylation of Organometallic Species with TrifluoromethanesulfanamidesPd‐Catalyzed Synthesis of ArSCF<sub>3</sub> Compounds under Mild ConditionsChemistry of novel compounds with a multifunctional carbon structure. 5. Molecular design of versatile building blocks for aliphatic monofluoro molecules by manipulation of multifunctional carbon structureCarbene-Induced Intra- vs Intermolecular Transfer-Fluoromethylation of Aryl Fluoromethylthio Compounds under Rhodium CatalysisDirect Catalytic Trifluoromethylthiolation of Boronic Acids and Alkynes Employing Electrophilic Shelf‐Stable <i>N</i>‐(trifluoromethylthio)phthalimideLewis Acid-Catalyzed Selective Mono-fluorination of Malonates Using Me-NFSIRh(III)-Catalyzed Trifluoromethylthiolation of Indoles via C–H ActivationTrifluoromethanesulfanylamides as Easy‐to‐Handle Equivalents of the Trifluoromethanesulfanyl Cation (CF<sub>3</sub>S<sup>+</sup>): Reaction with Alkenes and Alkynes<b>The Correlation of Biological Activity of Plant Growth Regulators and Chloromycetin Derivatives with Hammett Constants and Partition Coefficients</b>Selective and Scalable Synthesis of Trifluoromethanesulfenamides and Fluorinated Unsymmetrical Disulfides using a Shelf‐Stable Electrophilic SCF<sub>3</sub> ReagentNew approaches to enantioselective fluorination: Cinchona alkaloids combinations and chiral ligands/metal complexesTHALIDOMIDE AND CONGENITAL ABNORMALITIESElectrophilic Perfluoroalkylating AgentsOrganofluorine ChemistryThalidomide analogues: derivatives of an orphan drug with diverse biological activityTrifluoromethylsulfenylation of Masked Carbonyl CompoundsCopper-Catalyzed Intramolecular Oxytrifluoromethylthiolation of Unactivated AlkenesCopper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C–H Bonds via Nondirected Oxidative C(sp<sup>3</sup>)–H Activation9α-FLUORO DERIVATIVES OF CORTISONE AND HYDROCORTISONEN-Fluoro-3-ethyl-3-methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[e]1,2-thiazin-4-one, a new and efficient agent for electrophilic fluorination of carbanionsCopper-Catalyzed C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic TrifluoromethylationCopper‐Catalyzed Trifluoromethylation‐Initiated Radical 1,2‐Aryl Migration in α,α‐Diaryl Allylic AlcoholsMetal‐Free Direct Dehydroxytrifluoromethylthiolation of Alcohols via the Umpolung Reactivity of TrifluoromethanesulfenamidesIron-mediated Markovnikov-selective hydro-trifluoromethylthiolation of unactivated alkenesFluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)Elemental Fluorine and HOF·CH<sub>3</sub>CN in Service of General Organic ChemistryThe thalidomide sagaThalidomide: dermatological indications, mechanisms of action and side-effectsRecent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating ReagentsSequential Electrophilic Trifluoromethanesulfanylation–Cyclization of Tryptamine Derivatives: Synthesis of C(3)-Trifluoromethanesulfanylated Hexahydropyrrolo[2,3-<i>b</i>]indolesA facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenesTrifluoromethylthiolation of Aryl Iodides and Bromides Enabled by a Bench‐Stable and Easy‐To‐Recover Dinuclear Palladium(I) CatalystThe reaction of cyclic β-diketones with trifluoromethylsulphenyl chlorideDirect Trifluoromethylthiolation of Unactivated C(sp<sup>3</sup>)H Using Silver(I) Trifluoromethanethiolate and Potassium Persulfate6‐Trifluoromethyl‐Phenanthridines through Radical Trifluoromethylation of IsonitrilesA Fundamentally New Approach to Enantioselective Fluorination Based on Cinchona Alkaloid Derivatives/Selectfluor CombinationElectrophilic Trifluoromethanesulfanylation of Organometallic Species with TrifluoromethanesulfanamidesPreparation of Bis(β-trimethylsilylethanesulfonyl)imide and Its Use in the Synthesis of Protected Amine DerivativesCopper‐Catalyzed Intermolecular Trifluoromethylazidation of Alkenes: Convenient Access to CF<sub>3</sub>‐Containing Alkyl Azides(<i>R</i>)- and (<i>S</i>)-3-Fluorothalidomides: Isosteric Analogues of ThalidomideVisible‐Light‐Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide CatalysisVisible‐Light Photoredox‐Catalyzed Semipinacol‐Type Rearrangement: Trifluoromethylation/Ring Expansion by a Radical–Polar MechanismEnantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane‐Based Chiral SulfideNovel Methods for the Facile Construction of 3,3-Disubstituted and 3,3-Spiro-2<i>H</i>,4<i>H</i>-benzo[<i>e</i>]1,2-thiazine-1,1-diones: Synthesis of (11<i>S</i>,12<i>R</i>,14<i>R</i>)-2-Fluoro-14-methyl-11-(methylethyl)spiro[4<i>H</i>-benzo[<i>e</i>]- 1,2-thiazine-3,2‘-cyclohexane]-1,1-dione, an Agent for the Electrophilic Asymmetric Fluorination of Aryl Ketone EnolatesSandmeyer‐Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by CopperElectrophilic Trifluoromethylthiolation of Carbonyl CompoundsBenchmark and Solvent‐Free Preparation of Sulfonium Salt Based Electrophilic Trifluoromethylating Reagents2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one: Another Utility for Electrophilic Trifluoromethylthiolation ReactionsTrifluoromethylthiolation of Allylsilanes and Silyl Enol Ethers with Trifluoromethanesulfonyl Hypervalent Iodonium Ylide under Copper CatalysisAlkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and HeterocyclesThe Action of Elementary Fluorine Upon Organic Compounds. V<sup>1</sup>Copper-Promoted Sandmeyer Trifluoromethylation Reaction<i>N</i>‐Trifluoromethylthiosaccharin: An Easily Accessible, Shelf‐Stable, Broadly Applicable Trifluoromethylthiolating ReagentFluorination of methyl isobutyrate with perchloryl fluorideEffect of 3-Fluorothalidomide and 3-Methylthalidomide Enantiomers on Tumor Necrosis Factor Production and Antitumor Responses to the Antivascular Agent 5,6-Dimethylxanthenone-4-Acetic Acid (DMXAA)The evolution of thalidomide and its IMiD derivatives as anticancer agentsPhotoredoxkatalysierte Semipinakol‐Umlagerung mit sichtbarem Licht: Trifluormethylierung/Ringerweiterung über einen radikalisch‐polaren MechanismusThalidomide as a Multi‐Template for Development of Biologically Active Compounds(S)-form of alpha-methyl-N (alpha)-phthalimidoglutarimide, but not its (R)-form, enhanced phorbol ester-induced tumor necrosis factor-alpha production by human leukemia cell HL-60ChemInform Abstract: Novel Enantioselective Fluorinating Agents, (R)‐ and (S)‐N‐Fluoro‐3‐tert‐butyl‐7‐nitro‐3,4‐dihydro‐2H‐benzo[e][1,2]thiazine 1,1‐Dioxides.エナンチオ選択的フッ素化反応の新展開と含フッ素生理活性物質の合成不斉トリフルオロメチル化反応の開発Expeditious Synthesis of 3,4-Dihydro-2H-1.LAMBDA.6-benzo(e)(1,2)thiazine 1,1-Dioxides.
- References (URI)
- 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雑誌記事索引データベースCrossrefCiNii ArticlesCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossrefCrossref
- Bibliographic ID (NDL)
- 02771927511343269
- NAID
- 130005316052