Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides
The Journal of Organic ChemistryPublished 16 October 2013
Weijun Fu, Fengjuan Xu, Yuqin Fu, Mei Zhu, Jiaqi Yu, Xu Chen
Citations120
SJR quartileQ2
SJR score0.74
SNIP0.86
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
A mild and efficient visible-light-mediated diarylation of N-arylacrylamides with aryl diazonium salts under mild conditions has been developed and provides convenient access to a variety of useful 3,3-disubstituted oxindoles.
Abstract
A mild and efficient visible-light-mediated diarylation of N-arylacrylamides with aryl diazonium salts under mild conditions has been developed. This method provides convenient access to a variety of useful 3,3-disubstituted oxindoles by constructing two C-C bonds in one step.
Keywords
Chemistry
Chemical ReviewsVisible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
9,411 Citations2013Christopher K. Prier, Danica A. Rankic +1 more
The conversion of these bench stable, benign catalysts to redox-active species upon irradiation with simple household lightbulbs represents a remarkably chemoselective trigger to induce unique and valuable catalytic processes.
Chemical Society ReviewsVisible light photoredox catalysis: applications in organic synthesis
4,037 Citations2010Jagan M. R. Narayanam, Corey R. J. Stephenson
This tutorial review provides a historical overview of visible light photoredox catalysis in organic synthesis along with recent examples which underscore its vast potential to initiate organic transformations.
Nature ChemistryVisible light photocatalysis as a greener approach to photochemical synthesis
2,640 Citations2010Tehshik P. Yoon, Michael A. Ischay +1 more
Transition metal photocatalysis represents a promising strategy towards the development of practical, scalable industrial processes with great environmental benefits.
Angewandte Chemie International EditionPyrrolidinyl‐Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents
2,411 Citations2007Chris V. Galliford, Karl A. Scheidt
The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties.
Angewandte Chemie International EditionVisible‐Light Photoredox Catalysis
2,233 Citations2012Jun Xuan, Wen‐Jing Xiao
Recent advances made in this fast developing area of research are discussed in the Minireview of visible-light-promoted photocatalytic reactions.
European Journal of Organic ChemistryConstruction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids
1,444 Citations2003Christiane Marti, Erick M. Carreira
Advanced Synthesis & CatalysisCatalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position
1,248 Citations2010Feng Zhou, Yun‐Lin Liu +1 more
SynthesisAsymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products
1,059 Citations2009Barry M. Trost, Megan K. Brennan
This review highlights the advances in the literature up to May2009 in the synthesis of spirocyclic indoline natural products, including bothenantioselective and diastereoselectives methods.
Chemical Society ReviewsPhotoredox functionalization of C–H bonds adjacent to a nitrogen atom
1,042 Citations2012Lei Shi, Wujiong Xia
This tutorial review aims to give a brief overview of the functionalization of C-H bonds and the visible light photoredox catalysis and state the main results obtained in the reactions.
Angewandte Chemie International EditionThe Photocatalyzed Meerwein Arylation: Classic Reaction of Aryl Diazonium Salts in a New Light
787 Citations2013Durga Prasad Hari, Burkhard König
The origins of this reaction and its scope and applications are summarized and the use of photocatalyzed Pschorr cyclization to induce the one-electron reduction and activation of the diazonium salts is summarized.
Journal of the American Chemical SocietyMetal-Free, Visible-Light-Mediated Direct C–H Arylation of Heteroarenes with Aryl Diazonium Salts
784 Citations2012Durga Prasad Hari, Peter Schroll +1 more
The general and easy procedure provides a transition-metal-free alternative for the formation of aryl-heteroaryl bonds in heteroarenes by a photoredox process.
Chemical ReviewsRadical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical
776 Citations1988Carlo Galli
Journal of the American Chemical SocietyCombining Gold and Photoredox Catalysis: Visible Light-Mediated Oxy- and Aminoarylation of Alkenes
535 Citations2013Basudev Sahoo, Matthew N. Hopkinson +1 more
A room-temperature intramolecular oxy- and aminoarylation of alkenes with aryldiazonium salts has been developed using a novel gold and photoredox dual-catalytic system and demonstrates the potential of this system as a method to expand the scope of nucleophilic addition reactions to carbon-carbon multiple bonds.
Journal of the American Chemical SocietyPalladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature
486 Citations2011Xin Mu, Tao Wu +3 more
Organic & Biomolecular ChemistryRecent applications of arene diazonium salts in organic synthesis
462 Citations2013Fanyang Mo, Guangbin Dong +2 more
In this review, recent advances involving arene diazonium salts as starting materials or active intermediates for various synthetically useful applications are summarized.
Angewandte Chemie International EditionDirect Annulations toward Phosphorylated Oxindoles: Silver‐Catalyzed Carbon‐Phosphorus Functionalization of Alkenes
417 Citations2013Ya‐Min Li, Meng Sun +3 more
This paper aims to demonstrate the efforts towards in-situ applicability of EMMARM, as to provide real-time information about concrete mechanical properties such as E-modulus and compressive strength in the response of the immune system to EMTs.
Angewandte Chemie International EditionSynthesis of Oxindoles by Iron‐Catalyzed Oxidative 1,2‐Alkylarylation of Activated Alkenes with an Aryl C(sp<sup>2</sup>)H Bond and a C(sp<sup>3</sup>)H Bond Adjacent to a Heteroatom
393 Citations2013Wen‐Ting Wei, Mingbo Zhou +7 more
European Journal of Organic ChemistryTransition‐Metal‐Mediated Routes to 3,3‐Disubstituted Oxindoles through Anilide Cyclisation
313 Citations2011Johannes E. M. N. Klein, Richard J. K. Taylor
Angewandte Chemie International EditionPalladium‐Catalyzed Oxidative Arylalkylation of Activated Alkenes: Dual CH Bond Cleavage of an Arene and Acetonitrile
299 Citations2011Tao Wu, Xin Mu +1 more
Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate-determining C-H activation of the acetonitrile.
Chemistry - A European JournalIntermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts
294 Citations2008Markus R. Heinrich
This minireview is aimed at giving an overview of recent advances in olefin functionalisation reactions involving aryl radicals generated from arenediazonium salts.
Angewandte Chemie International EditionMetal‐Free Radical Azidoarylation of Alkenes: Rapid Access to Oxindoles by Cascade CN and CC Bond‐Forming Reactions
279 Citations2013Kiran Matcha, Rishikesh Narayan +1 more
Chemical ScienceMetal-free oxidative tandem coupling of activated alkenes with carbonyl C(sp2)–H bonds and aryl C(sp2)–H bonds using TBHP
273 Citations2013Mingbo Zhou, Ren‐Jie Song +5 more
This method allows 1,2-difunctionalization of the C–C double bond in N-arylacrylamides by simultaneous formation of two C(sp2)–C(sp3) bonds.
Angewandte Chemie International EditionOxindole Synthesis by Direct Coupling of CH and CH Centers
271 Citations2009Yi‐Xia Jia, E. Peter Kündig
An sp(2)/sp(3) get-together: A novel and efficient method can be used to synthesize 3,3-disubstitued oxindoles by the direct intramolecular oxidative coupling of an aryl C(sp(2)-H and a C(3))-H center (see scheme).
Journal of the American Chemical SocietyThe Palladium Catalyzed Asymmetric Addition of Oxindoles and Allenes: An Atom-Economical Versatile Method for the Construction of Chiral Indole Alkaloids
262 Citations2011Barry M. Trost, Jia Xie +1 more
It is demonstrated that allenes can be used to generate the reactive Pd(π-allyl) intermediate in the presence of an acid cocatalyst, and this system is compatible with nucleophiles to allow for formation of formal AAA products by Pd-catalyzed additions to allenes.
Chemical CommunicationsA room temperature decarboxylation/C–H functionalization cascade by visible-light photoredox catalysis
260 Citations2013Jin Xie, Xu Pan +5 more
An elegant approach to quaternary oxindole formation has been developed through a room temperature decarboxylation/radical C-H functionalization by visible-light photoredox catalysis.
ChemCatChemDyes as Visible Light Photoredox Organocatalysts
245 Citations2011Davide Ravelli, Maurizio Fagnoni
Angewandte Chemie International EditionActivation of a C(sp<sup>3</sup>)H Bond by a Transient σ‐Alkylpalladium(II) Complex: Synthesis of Spirooxindoles Through a Palladium‐Catalyzed Domino Carbopalladation/C(sp<sup>3</sup>)C(sp<sup>3</sup>) Bond‐Forming Process
198 Citations2012Tiffany Piou, Luc Neuville +1 more
Palladium-catalyzed activation of C(sp3)-H bond by a σ-alkyl Pd(II) complex generated in situ from a remote arylhalide function is developed.
The Journal of Organic ChemistrySynthesis of Sulfonated Oxindoles by Potassium Iodide Catalyzed Arylsulfonylation of Activated Alkenes with Sulfonylhydrazides in Water
198 Citations2013Xiaoqing Li, Xiangsheng Xu +3 more
A catalytic system consisting of KI, 18-crown-6, and TBHP for arylsulfonylation of activated alkenes with sulfonylhydrazides as sulfonyL precursor is described, providing a practical and environmentally benign method for the construction of sulfonated oxindoles in water.
Organic LettersPalladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles
196 Citations2010Stéphanie Jaegli, Jérémy Dufour +6 more
A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivatives involving concomitant direct C-H functionalization and C-X bond formation was developed by simply changing the reaction conditions.
The Journal of Organic ChemistryVisible-Light-Mediated α-Arylation of Enol Acetates Using Aryl Diazonium Salts
183 Citations2012Thea Hering, Durga Prasad Hari +1 more
Visible light mediates efficiently the α-arylation of enol acetates by aryl diazonium salts under mild conditions using [Ru(bpy)(3)]Cl(2) as a photoredox catalyst.
Chemical CommunicationsMetal-free oxidative hydroxyalkylarylation of activated alkenes by direct sp3 C–H functionalization of alcohols
168 Citations2013Yuan Meng, Li‐Na Guo +2 more
A metal-free tandem radical addition/cyclization reaction of activated alkenes and alcohols has been developed that provides an efficient and atom economical access to various valuable hydroxyl-containing oxindoles through the direct sp(3) C-H functionalization of alcohols.
Advanced Synthesis & CatalysisSilver‐Catalyzed Decarboxylative Acylarylation of Acrylamides with α‐Oxocarboxylic Acids in Aqueous Media
163 Citations2013Hua Wang, Lina Guo +1 more
Chemical CommunicationsSilver-catalyzed oxidative coupling/cyclization of acrylamides with 1,3-dicarbonyl compounds
157 Citations2013Hua Wang, Li‐Na Guo +1 more
An efficient silver-catalyzed oxidative cyclization of acrylamides with 1,3-dicarbonyl compounds is described, which proceeds through a tandem radical addition/cyclization process, in which two new C-C bonds were formed.
Chemistry - A European JournalAryl Radical Formation by Copper(I) Photocatalyzed Reduction of Diaryliodonium Salts: NMR Evidence for a Cu<sup>II</sup>/Cu<sup>I</sup> Mechanism
156 Citations2013Alexandre Baralle, Louis Fensterbank +2 more
Advanced Synthesis & CatalysisPhenanthrene Synthesis by Eosin Y‐Catalyzed, Visible Light‐ Induced [4+2] Benzannulation of Biaryldiazonium Salts with Alkynes
155 Citations2012Tiebo Xiao, Xichang Dong +2 more
Journal of the American Chemical SocietyRadical Additions of Aryl Iodides to Arenes Are Facilitated by Oxidative Rearomatization with Dioxygen
155 Citations2006Dennis P. Curran, Adam I. Keller
A chain mechanism involving reaction of the intermediate cyclohexadienyl radical with oxygen to directly generate the aromatized product and the hydroperoxy radical is proposed.
Chemistry - A European JournalCopper‐Catalyzed Oxidative Benzylarylation of Acrylamides by Benzylic CH Bond Functionalization for the Synthesis of Oxindoles
146 Citations2013Shi‐Liu Zhou, Li‐Na Guo +2 more
An efficient method for the benzylarylation of activated alkenes has been developed through a copper-catalyzed tandem radical addition/cyclization strategy, which provides access to diverse alkyl-substituted oxindoles in good to excellent yields.
ChemistryOpenPhotocatalytic Arylation of Alkenes, Alkynes and Enones with Diazonium Salts
144 Citations2012Peter Schroll, Durga Prasad Hari +1 more
Teaching old dogs new tricks: Visible light photoredox catalysis improves the classic Meerwein arylation protocol significantly and allows the light-controlled arylations of alkenes, alkynes and enones by diazonium salts.
Organic LettersPhenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides
139 Citations2012Junwei Wang, Yucheng Yuan +4 more
The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO( 2)Et) in CF(3)CH(2)OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilide 1' afforded the C(2)-Symmetric or unsymmetric spirooxindoles 3.
Organic LettersSilver-Catalyzed Carboazidation of Arylacrylamides
137 Citations2013Xiaohong Wei, Ya‐Min Li +3 more
A novel and inexpensive method of nontoxic, silver-salt-catalyzed carboazidation of arylacrylamides to afford corresponding azide oxindoles is reported, which exhibits great functional group tolerance.
Chemistry - A European JournalMetal‐Free Synthesis of 3,3‐Disubstituted Oxoindoles by Iodine(III)‐Catalyzed Bromocarbocyclizations
132 Citations2012David C. Fabry, M. Stodulski +2 more
An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles and can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
Chemistry - A European JournalA Mild Oxidative Aryl Radical Addition into Alkenes by Aerobic Oxidation of Arylhydrazines
116 Citations2011Tsuyoshi Taniguchi, Hisaaki Zaimoku +1 more
A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds by using potassium ferrocyanide trihydrate and water.
Organic LettersIodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles
112 Citations2011Hai‐Long Wei, Tiffany Piou +3 more
Chemical CommunicationsOxindole synthesis by palladium-catalysed aromatic C–H alkenylation
110 Citations2010Satoshi Ueda, Takahiro Okada +1 more
A strategy involving palladium-catalysed aromatic C-H functionalisation/intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles in moderate to good yield.
Organic LettersTransition-Metal-Free Synthesis of Oxindoles by Potassium <i>tert</i>-Butoxide-Promoted Intramolecular α-Arylation
104 Citations2012Astrid Beyer, Julien Buendia +1 more
Potassium tert-butoxide-mediated intramolecular α-arylations of fluoro- and chloro-substituted anilides provide oxindoles in DMF at 80 °C in moderate to high yields.
Organic LettersSynthesis of Chiral <i>N</i>-Heterocyclic Carbene Ligands with Rigid Backbones and Application to the Palladium-Catalyzed Enantioselective Intramolecular α-Arylation of Amides
101 Citations2011Lantao Liu, Naoki Ishida +2 more
Chiral N-heterocyclic carbene ligands having a 2,2'-bisquinoline-based C(2) symmetric skeleton were developed and exhibited good enantioselectivity in palladium-catalyzed intramolecular α-arylation of amides to give 3,3-disubsituted oxindoles.
Topics in current chemistryRadicals in Synthesis III
89 Citations2012Heinrich, Markus, Gansäuer, Andreas
Chemistry - An Asian JournalAg‐Promoted Azido‐Carbocyclization of Activated Alkenes via CH Bond Cleavage
83 Citations2013Yizhi Yuan, Tao Shen +2 more
Angewandte Chemie International EditionThree‐Component Metal‐Free Arylation of Isocyanides
69 Citations2013M. V. Basavanag Unnamatla, Laurent El Kaïm +3 more
The formation of a metal/aryl complex starting from aryl iodide or bromide is followed by isocyanide insertion and trapping of the metal/imidoyl complex with various nucleophiles, which results in three-component couplings.
Chemical CommunicationsAza-oxindole synthesis by oxidative coupling of Csp2–H and Csp3–H centers
36 Citations2012Chandan Dey, E. Peter Kündig
A Cu(II) mediated oxidative C(sp(2)-H and C(3))-H coupling protocol gives access to aza-oxindoles in good to excellent yield in the presence of NaOtBu as base and toluene as solvent.
Journal of Organometallic ChemistryPalladium catalysed tandem cyclisation–anion capture processes. Part 8 : In situ and preformed organostannanes. Carbamyl chlorides and other starter species
32 Citations2006Anwar Usman, Mark R. Fielding +3 more
A sequential one-pot process involving in situ, palladium catalysed, formation of a series of tributylstannyl-1,2-carbo and heterocyclic dialkylidene-5-membered rings from the corresponding 1,6-diynes and Bu 3 SnH affording a diverse range of heterocycles in good yield.
Helvetica Chimica ActaAzirine/Oxindole Ring Enlargement <i>via</i> Amidinium Intermediates
15 Citations2004Maged K. G. Mekhael, Stefan Bienz +2 more
