4.7 Article

Visible-Light-Induced Transition-Metal-Free Nitrogen-Centered Radical Strategy for the Synthesis of 2-Acylated 9H-Pyrrolo[1,2-a]indoles

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Visible Light-Driven Radical-Mediated C-C Bond Cleavage/Functionalization in Organic Synthesis

Xiao-Ye Yu et al.

Summary: In recent years, visible light photoredox-catalyzed radical-mediated C-C bond cleavage reactions have emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C-C bond cleavage in diverse molecular scaffolds. These reactions provide an efficient way to construct structurally diverse molecular skeletons, contributing to the development in the field of synthetic organic chemistry.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

Dual Photoredox/Palladium-Catalyzed C-H Acylation of 2-Arylpyridines with Oxime Esters

Bin-Qing He et al.

Summary: An unprecedented dual photoredox/palladium-catalyzed reaction using oxime esters for C-C bond cleavage and directed ortho C-H acylation of 2-arylpyridines has been described. This redox-neutral protocol demonstrates excellent regioselectivity, broad substrate scope, and good functional-group tolerance, resulting in a range of aryl ketones with generally good yields.

SYNLETT (2021)

Review Chemistry, Applied

Recent Developments in Radical Cross-Coupling of Redox-Active Cycloketone Oximes

Fang Xiao et al.

Summary: A new method has been discovered to introduce active cyanoalkyl groups into organic compounds via ring fragmentation without the use of toxic cyanide sources. Recent advances in redox-active cycloketone oximes-based cross-couplings were comprehensively reviewed, categorizing into non-photocatalyzed and photocatalyzed cross-couplings with representative examples and reaction mechanisms discussed.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Organic

Copper-Catalyzed Radical Aryl Migration Approach for the Preparation of Cyanoalkylsulfonylated Oxindoles/Cyanoalkyl Amides

Ming Li et al.

Summary: The copper-catalyzed radical cross-coupling of oxime esters and activated alkenes successfully produced cyanoalkylsulfonylated oxindoles and cyanoalkyl amides through an aryl migration strategy, with unique desulfonylation and sulfone addition processes involved. The transformation demonstrates good functional group applicability, enabling the regioselective control of two different quaternary stereocenters by the substituent group of the nitrogen atom.

ORGANIC LETTERS (2021)

Review Chemistry, Applied

Oxime-Derived Iminyl Radicals in Selective Processes of Hydrogen Atom Transfer and Addition to Carbon-Carbon π-Bonds

Igor B. Krylov et al.

Summary: This review focuses on synthetic methods based on oxime-derived iminyl radicals developed in the last few years, excluding ring opening reactions of cyclic iminyl radicals summarized in recent publications. It highlights reactions involving 1,n-hydrogen atom transfer and addition of iminyl radicals to the carbon-carbon pi-bond, showcasing the versatility and utility of these methods in organic synthesis.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Multidisciplinary Sciences

Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis

Peng-Zi Wang et al.

Summary: The radical vicinal dicarbofunctionalization (DCF) reaction of olefins by merging of radical addition and cross-coupling using photoredox and copper dual catalysis demonstrates high enantioselectivity and tolerance towards a wide range of functionalities. This protocol provides a valuable synthetic tool for the construction of optically active compounds with potential applications in organic synthesis.

NATURE COMMUNICATIONS (2021)

Review Chemistry, Organic

One-Electron Reduction of Redox-Active Esters to Generate Carbon-Centered Radicals

Pengfei Niu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

A Radical Smiles Rearrangement Promoted by Neutral Eosin Y as a Direct Hydrogen Atom Transfer Photocatalyst

Jianming Yan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Photocatalytic Hydroacylation of Alkenes by Directly Using Acyl Oximes

Lan Zheng et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Editorial Material Chemistry, Multidisciplinary

New Roles for Photoexcited Eosin Y in Photochemical Reactions

Dong-Mei Yan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Synthesis of 2-Sulfonated-9H-Pyrrolo[1,2-a]indoles via a Ag-Promoted Cascade Sulfonation and Cyclization

Xiaoyu Xie et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Direct C-H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C-C Bond Cleavage

Lin Yang et al.

ORGANIC LETTERS (2018)

Article Chemistry, Applied

Copper-Catalyzed Radical Sulfonylation of N-Propargylindoles with Concomitant 1,2-Aryl Migration

Xin-Yu Zhu et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Review Chemistry, Applied

N-(Acyloxy)phthalimides as Redox-Active Esters in Cross-Coupling Reactions

Sandip Murarka

ADVANCED SYNTHESIS & CATALYSIS (2018)

Article Multidisciplinary Sciences

A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes

Muliang Zhang et al.

NATURE COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids

Xiao-Ye Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades

Elizabeth M. Dauncey et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

A Visible-Light-Driven Iminyl Radical-Mediated C-C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters

Xiao-Ye Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters

Wei Ding et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Radical 1,2-Alkylarylation/Acylarylation of Allylic Alcohols with Aldehydes via Neophyl Rearrangement

Changduo Pan et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis

Xiaheng Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Wade F. Petersen et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

Article Chemistry, Organic

Visible Light as a Sole Requirement for Intramolecular C(sp3)-H Imination

Jingjing Li et al.

ORGANIC LETTERS (2017)

Article Chemistry, Physical

Nickel-Catalyzed 1,2-Aminoarylation of Oxime Ester-Tethered Alkenes with Boronic Acids

Hai-Bin Yang et al.

ACS CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Alkynylation of Csp2(O)-H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer

Satobhisha Mukherjee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes

Fredrik Pettersson et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade

Wei Shu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers

Hai-Bin Yang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Review Chemistry, Multidisciplinary

Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond

Jia-Rong Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Multidisciplinary

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

Hanchu Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions

Jacob Davies et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids

Lingling Chu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis

Giulia Bergonzini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines

Heng Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2

Jie Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts

Heng Jiang et al.

CHEMICAL COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

The Photocatalyzed Meerwein Arylation: Classic Reaction of Aryl Diazonium Salts in a New Light

Durga Prasad Hari et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

Phillip D. Bass et al.

CHEMICAL REVIEWS (2013)

Article Chemistry, Multidisciplinary

Dissociation or Cyclization: Options for a Triad of Radicals Released from Oxime Carbamates

Roy T. McBurney et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Chemistry, Multidisciplinary

Visible-Light Photoredox Catalysis

Jun Xuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Organocatalytic umpolung: N-heterocyclic carbenes and beyond

Xavier Bugaut et al.

CHEMICAL SOCIETY REVIEWS (2012)

Article Chemistry, Multidisciplinary

Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts

Durga Prasad Hari et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

Roy T. McBurney et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Multidisciplinary

Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides

Weiping Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Biochemistry & Molecular Biology

Minisci reactions: Versatile CH-functionalizations for medicinal chemists

Matthew A. J. Duncton

MEDCHEMCOMM (2011)

Article Chemistry, Multidisciplinary

Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids

Ping Fang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Biochemistry & Molecular Biology

Potent antitumor bifunctional DNA alkylating agents, synthesis and biological activities of 3a-aza-cyclopenta[a]indenes

Rajesh Kakadiya et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2009)

Article Chemistry, Multidisciplinary

From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals

Fernando Portela-Cubillo et al.

CHEMICAL COMMUNICATIONS (2008)

Article Chemistry, Organic

Thermal rearrangement of indolyl oxime esters to pyridoindoles

Fernando Portela-Cubillo et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

Review Chemistry, Multidisciplinary

Organocatalysis by N-heterocyclic, carbenes

Dieter Enders et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Multidisciplinary

Chemoselective benzylic C-H Activations for the preparation of condensed N-heterocycles

Hongjun Ren et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Review Chemistry, Multidisciplinary

Antitumor antibiotics: Bleomycin, endiynes, and mitomycin

U Galm et al.

CHEMICAL REVIEWS (2005)

Review Chemistry, Multidisciplinary

Mechanisms of in situ activation for DNA-targeting antitumor agents

SE Wolkenberg et al.

CHEMICAL REVIEWS (2002)

Article Chemistry, Organic

Generation and intermolecular reactions of 2-indolylacyl radicals

ML Bennasar et al.

ORGANIC LETTERS (2001)

Article Chemistry, Multidisciplinary

Palladium(0)-catalyzed ring cleavage of cyclobutanone grimes leading to nitriles via β-carbon elimination

T Nishimura et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)