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巻号45 (8)
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Silver-catalyzed vinylic C-F bond activation : synthesis of 2-fluoroindoles from β,β-difluoro-o-sulfonamidostyrenes

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Silver-catalyzed vinylic C-F bond activation : synthesis of 2-fluoroindoles from β,β-difluoro-o-sulfonamidostyrenes

国立国会図書館永続的識別子
info:ndljp/pid/11459678
資料種別
記事
著者
Takeshi Fujitaほか
出版者
The Chemical Society of Japan
出版年
2016-05-20
資料形態
デジタル
掲載誌名
Chemistry letters 45(8)
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要約等:

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...

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デジタル

資料種別
記事
著者・編者
Takeshi Fujita
Yota Watabe
Shigeyuki Yamashita
出版年月日等
2016-05-20
出版年(W3CDTF)
2016-05-20
タイトル(掲載誌)
Chemistry letters
巻号年月日等(掲載誌)
45(8)
掲載巻
45(8)
ISSN(掲載誌)
1348-0715
ISSN-L(掲載誌)
0366-7022
本文の言語コード
eng
国立国会図書館永続的識別子
info:ndljp/pid/11459678
コレクション(共通)
コレクション(障害者向け資料:レベル1)
コレクション(個別)
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
収集根拠
オンライン資料収集制度
受理日(W3CDTF)
2020-03-13T20:40:24+09:00
保存日(W3CDTF)
2020-03-13
記録形式(IMT)
application/pdf
オンライン閲覧公開範囲
国立国会図書館内限定公開
デジタル化資料送信
図書館・個人送信対象外
遠隔複写可否(NDL)
掲載誌(国立国会図書館永続的識別子)
info:ndljp/pid/11459665
連携機関・データベース
国立国会図書館 : 国立国会図書館デジタルコレクション

デジタル

要約等
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
オンライン閲覧公開範囲
インターネット公開
連携機関・データベース
科学技術振興機構 : J-STAGE

デジタル

要約等
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.
参照
Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Brønsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3‐Hexafluoropropan‐2‐ol
Aluminium-mediated aromatic C-F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks
Construction of Pinpoint-Fluorinated Benzothiophene Frameworks Using Palladium-Catalyzed Cyclization of o-(Fluorovinyl)phenyl-Substituted Thiophenes
Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes
Nucleophilic 5-endo-trig cyclization of 2-(trifluoromethyl)allylic metal enolates and enamides: Synthesis of tetrahydrofurans and pyrrolidines bearing exo-difluoromethylene units
Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation
Highly Active Cross-Metathesis of Tetrafluoroethylene with a Seven-Membered N-Heterocyclic-Carbene–Ruthenium Catalyst
Synthesis of 3‐CF<sub>3</sub>‐Indoles from HFO‐1234ze(<i>E</i>) via Cross‐Coupling and Intramolecular Cyclization
Synthesis of 3‐(Trifluoromethyl)indoles by Oxidative Cyclization of <i>o</i>‐Sulfonamido‐α‐(trifluoromethyl)styrenes
Transition‐Metal‐Mediated and ‐Catalyzed C−F Bond Activation by Fluorine Elimination
Lewis 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
参照
Efficient double bond migration of allylbenzenes catalyzed by Pd(OAc)_2-HFIP system with unique substituent effect
Catalytic defluorinative [3 + 2] cycloaddition of trifluoromethylalkenes with alkynes via reduction of nickel(<scp>ii</scp>) fluoride species
Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Ketone Enolates: Synthesis of 5-Fluorinated 2-Alkylidene-2,3-dihydrofurans
Domino Friedel–Crafts‐Type Cyclizations of Difluoroalkenes Promoted by the α‐Cation‐Stabilizing Effect of Fluorine: An Efficient Method for Synthesizing Angular PAHs
Catalytic Transformations of Fluorinated Olefins
Concise Synthesis of Halogenated Chrysenes ([4]Phenacenes) that Favor π-Stack Packing in Single Crystals
Heck-type 5-endo-trig cyclizations promoted by vinylic fluorines: Ring-fluorinated indene and 3H-pyrrole syntheses from 1,1-difluoro-1-alkenes
Heck-type 5-endo-trig cyclization promoted by vinylic fluorines: synthesis of 5-fluoro-3H-pyrroles
Synthesis of Exocyclic Trisubstituted Alkenes <i>via</i> Nickel‐ Catalyzed Kumada‐Type Cross‐Coupling Reaction of <i>gem</i>‐ Difluoroalkenes with Di‐Grignard Reagents
Efficient Helicene Synthesis: Friedel–Crafts‐type Cyclization of 1,1‐Difluoro‐1‐alkenes
CF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl‐3,5‐diaryl‐2‐oxazolidinones by Desymmetrization of 2‐Aryl‐1,3‐difluoropropan‐2‐ols
Method for the Synthesis of Dibenzo[<i>g</i>,<i>p</i>]Chrysenes: Domino Friedel–Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups
A Synthesis of Dihydrofuran-3(2<i>H</i>)-ones
5-Endo-trigonal reactions: a disfavoured ring closure
Pd-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-ones
Rhodium-catalysed C(sp2)–C(sp2) bond formation via C–H/C–F activation
Copper-Catalyzed <i>gem</i>-Difluoroolefination of Diazo Compounds with TMSCF<sub>3</sub> via C–F Bond Cleavage
Synthesis of <i>gem</i>-Difluoroalkenes via β-Fluoride Elimination of Organorhodium(I)
Double CF Bond Activation through β‐Fluorine Elimination: Nickel‐Mediated [3+2] Cycloaddition of 2‐Trifluoromethyl‐1‐alkenes with Alkynes
Pinpoint-fluorinated phenanthrene synthesis based on C F bond activation of difluoroalkenes
Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles
Activation of 1,1-Difluoro-1-alkenes with a Transition-Metal Complex:  Palladium(II)-Catalyzed Friedel–Crafts-Type Cyclization of 4,4-(Difluorohomoallyl)arenes
Lewis 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‐dihydroquinazolines
Nickel-Catalyzed Allylic C(sp<sup>3</sup>)–F Bond Activation of Trifluoromethyl Groups via β-Fluorine Elimination: Synthesis of Difluoro-1,4-dienes
Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies
Palladium- and Nickel-Catalyzed Kumada Cross-Coupling Reactions of <i>gem</i>-Difluoroalkenes and Monofluoroalkenes with Grignard Reagents
Diastereoselective Intramolecular Allyl Transfer from Allyl Carbamate Accompanied by 5‐<i>endo</i>‐trig Ring Closure
Friedel-Crafts Cyclization of 1,1-Difluoroalk-1-enes: Synthesis of Benzene-Fused Cyclic Ketones via α-Fluorocarbocations
Cu(I)-Catalyzed Cross-Coupling of Terminal Alkynes with Trifluoromethyl Ketone <i>N</i>-Tosylhydrazones: Access to 1,1-Difluoro-1,3-enynes
Ring constructions by the use of fluorine substituent as activator and controller
Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C–F Bond Activation To Access Fluorinated Building Blocks
Fluorinated Alcohols: A New Medium for Selective and Clean Reaction
A Robust, Well‐Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2‐Ethynylanilines Leading to Indoles
Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis
Rules for ring closure
C−F Bond Activation in Organic Synthesis
Vinylic CF bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconocene
Fluorine-Directed Nazarov Cyclizations: A Controlled Synthesis of Cross-Conjugated 2-Cyclopenten-1-ones
Reactions of 1,1-difluoro-1-olefins with electrophilic reagents
5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes: synthesis of 4-difluoromethylene-substituted 1-pyrrolines
Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts
Significant Enhancement in the Efficiency and Selectivity of Iron‐Catalyzed Oxidative Cross‐Coupling of Phenols by Fluoroalcohols
Synthesis of fluorostyrenes via palladium‐catalyzed reactions of aromatic halides with fluoroolefins
Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine
An 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 Arenes
Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding
Fluorinated alcohols: A magic medium for the synthesis of heterocyclic compounds
The 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 Process
Intramolecular 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>-swainsonine
Friedel−Crafts-Type Cyclization of 2,2-Difluorovinyl Ketones via α-Fluorocarbocations and Its Application in Domino Cyclizations
Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose
Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
Pd‐Catalyzed Regioselective Activation of <i>gem</i>‐Difluorinated Cyclopropanes: A Highly Efficient Approach to 2‐Fluorinated Allylic Scaffolds
Electrophilic 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 Amination
Copper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate
連携機関・データベース
国立情報学研究所 : CiNii Research
書誌ID(NDLBibID)
11459678
NII論文ID
130005254491