C4–H indole functionalisation: precedent and prospects

Weak Directing Group Steered Formal Oxidative [2+2+2]-Cyclization for Selective Benzannulation of Indoles

(2018) Kiran R. Bettadapur et al.   JOURNAL OF ORGANIC CHEMISTRY

Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis

(2018) Parthasarathy Gandeepan et al.   Chem

Diverse ortho-C(sp2)–H Functionalization of Benzaldehydes Using Transient Directing Groups

(2017) Xi-Hai Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Recent advances in fluoride-free aryne generation from arene precursors

(2017) Fahima I. M. Idiris et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Recent progress in transition-metal-catalyzed enantioselective indole functionalizations

(2017) Jing-Biao Chen et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (−)-Agroclavine and (−)-Elymoclavine

(2017) Jianbo Lv et al.   ORGANIC LETTERS

Rhodium-Catalyzed Site-Selective Coupling of Indoles with Diazo Esters: C4-Alkylation versus C2-Annulation

(2017) Xiaohong Chen et al.   ORGANIC LETTERS

Iridium-Catalyzed Direct Regioselective C4-Amidation of Indoles under Mild Conditions

(2017) Shuyou Chen et al.   ORGANIC LETTERS

Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies

(2017) Michael A. Corsello et al.   Chemical Science

Remote C6-Selective Ruthenium-Catalyzed C–H Alkylation of Indole Derivatives via σ-Activation

(2017) Jamie A. Leitch et al.   ACS Catalysis

Beyond C2 and C3: Transition-Metal-Catalyzed C–H Functionalization of Indole

(2017) Jamie A. Leitch et al.   ACS Catalysis

Aryne Insertion into σ Bonds

(2017) Manjoorahmed Asamdi et al.   Asian Journal of Organic Chemistry

One-pot synthesis of fluorescent 2,4-dialkenylindoles by rhodium-catalyzed dual C–H functionalization

(2017) Hui Chen et al.   Organic Chemistry Frontiers

Manganese(I)-Catalyzed Substitutive C−H Allylation

(2016) Weiping Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ru-catalysed C–H silylation of unprotected gramines, tryptamines and their congeners

(2016) K. Devaraj et al.   CHEMICAL COMMUNICATIONS

Organic Photoredox Catalysis

(2016) Nathan A. Romero et al.   CHEMICAL REVIEWS

Synthesis of biaryls using aryne intermediates

(2016) José-Antonio García-López et al.   CHEMICAL SOCIETY REVIEWS

Mild metal-catalyzed C–H activation: examples and concepts

(2016) T. Gensch et al.   CHEMICAL SOCIETY REVIEWS

The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

(2016) Tim Cernak et al.   CHEMICAL SOCIETY REVIEWS

Recent Advances in Gold-Catalyzed Intermolecular Aryl C−H Functionalization

(2016) Søren Kramer   CHEMISTRY-A EUROPEAN JOURNAL

Ruthenium(II) Biscarboxylate-Catalyzed Borylations of C(sp2 )−H and C(sp3 )−H Bonds

(2016) Suman De Sarkar et al.   CHEMISTRY-A EUROPEAN JOURNAL

Ruthenium-Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides

(2016) Marco Simonetti et al.   CHEMISTRY-A EUROPEAN JOURNAL

Recent Advances in C–H Functionalization

(2016) Huw M. L. Davies et al.   JOURNAL OF ORGANIC CHEMISTRY

Photoredox Catalysis in Organic Chemistry

(2016) Megan H. Shaw et al.   JOURNAL OF ORGANIC CHEMISTRY

Concise total synthesis of (±)-serotobenine

(2016) Kangjiang Liang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles

(2016) Veeranjaneyulu Lanke et al.   ORGANIC LETTERS

Rh(III)-Catalyzed Aryl and Alkenyl C–H Bond Addition to Diverse Nitroalkenes

(2016) Tyler J. Potter et al.   ACS Catalysis

Manganese-Catalyzed C–H Activation

(2016) Weiping Liu et al.   ACS Catalysis

Radical-based regioselective cross-coupling of indoles and cycloalkanes

(2016) Jianmin Xiu et al.   Catalysis Science & Technology

Iron-Catalyzed C–H Functionalization Processes

(2016) Gianpiero Cera et al.   Topics in Current Chemistry

Nickel-Catalyzed Aromatic C–H Functionalization

(2016) Junichiro Yamaguchi et al.   Topics in Current Chemistry

Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds

(2015) Olafs Daugulis et al.   ACCOUNTS OF CHEMICAL RESEARCH

Transition Metal-Catalyzed CH Activation of Indoles

(2015) Alexander H. Sandtorv   ADVANCED SYNTHESIS & CATALYSIS

A Concise and Scalable Strategy for the Total Synthesis of Dictyodendrin B Based on Sequential CH Functionalization

(2015) Andrew K. Pitts et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic meta-selective C–H functionalization to construct quaternary carbon centres

(2015) Andrew J. Paterson et al.   CHEMICAL COMMUNICATIONS

Manganese catalyzed C–H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity

(2015) Lijun Shi et al.   CHEMICAL COMMUNICATIONS

Strategies for the asymmetric functionalization of indoles: an update

(2015) Renato Dalpozzo   CHEMICAL SOCIETY REVIEWS

Ru-Catalysed CH Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies

(2015) Carina Sollert et al.   CHEMISTRY-A EUROPEAN JOURNAL

Concise Syntheses of Dictyodendrins A and F by a Sequential C–H Functionalization Strategy

(2015) Atsushi D. Yamaguchi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cobalt-Catalyzed C–H Activation

(2015) Marc Moselage et al.   ACS Catalysis

Phosphine-Directed CH Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters

(2014) Kristina M. Crawford et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-Catalyzed C–H Functionalization Reactions: Efficient Synthesis of Heterocycles

(2014) Xun-Xiang Guo et al.   CHEMICAL REVIEWS

C–H Functionalization in the Synthesis of Amino Acids and Peptides

(2014) Anaïs F. M. Noisier et al.   CHEMICAL REVIEWS

Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents

(2014) Julie Charpentier et al.   CHEMICAL REVIEWS

Arene C–H functionalisation using a removable/modifiable or a traceless directing group strategy

(2014) Fengzhi Zhang et al.   CHEMICAL SOCIETY REVIEWS

Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents

(2014) Sebastián Barata-Vallejo et al.   CHEMISTRY-A EUROPEAN JOURNAL

Total Synthesis of Dictyodendrins B and E, and Formal Synthesis of Dictyodendrin C

(2014) Pengyu Tao et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Tuning Reactivity and Site Selectivity of Simple Arenes in C–H Activation: Ortho-Arylation of Anisoles via Arene–Metal π-Complexation

(2014) Paolo Ricci et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Beyond Directed ortho Metalation: Ru-Catalyzed CAr–O Activation/Cross-Coupling Reaction by Amide Chelation

(2014) Yigang Zhao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Iridium-Catalyzed C–H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism

(2014) Matthew A. Larsen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biosynthesis of the ergot alkaloids

(2014) Dorota Jakubczyk et al.   NATURAL PRODUCT REPORTS

Recent advances in homogeneous nickel catalysis

(2014) Sarah Z. Tasker et al.   NATURE

Synthesis of Unique Analogues of the Ergoline Skeleton Using Intramolecular [3+2] Cycloaddition

(2014) Frédéric Lecornué et al.   SYNLETT

Unexpected regioselective carbon–hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles

(2014) Xingyan Liu et al.   Nature Communications

The Witkop Cyclization: A Photoinduced CH Activation of the Indole System

(2013) Philipp J. Gritsch et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Synthesis of Dictyodendrins B and E

(2013) Jingjing Liang et al.   JOURNAL OF ORGANIC CHEMISTRY

Arene–Metal π-Complexation as a Traceless Reactivity Enhancer for C–H Arylation

(2013) Paolo Ricci et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

meta-Selective C–H Bond Alkylation with Secondary Alkyl Halides

(2013) Nora Hofmann et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biomedical Importance of Indoles

(2013) Nagendra Kaushik et al.   MOLECULES

C–H bond activation enables the rapid construction and late-stage diversification of functional molecules

(2013) Joanna Wencel-Delord et al.   Nature Chemistry

Direct Olefination at the C-4 Position of Tryptophan via C–H Activation: Application to Biomimetic Synthesis of Clavicipitic Acid

(2013) Qiang Liu et al.   ORGANIC LETTERS

Regioselective Synthesis of 4-Substituted Indoles via C–H Activation: A Ruthenium Catalyzed Novel Directing Group Strategy

(2013) Veeranjaneyulu Lanke et al.   ORGANIC LETTERS

How to ‘Cope' with the Prenylation of the Indole C4 Position

(2013) Tanja Gaich et al.   SYNLETT

Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process

(2012) Darius D. Schwarzer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

An Efficient Computational Model to Predict the Synthetic Utility of Heterocyclic Arynes

(2012) Adam E. Goetz et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Indigo and Tyrian Purple - From Ancient Natural Dyes to Modern Organic Semiconductors

(2012) Eric Daniel Głowacki et al.   ISRAEL JOURNAL OF CHEMISTRY

Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

(2012) Paul A. Vadola et al.   JOURNAL OF ORGANIC CHEMISTRY

Cytochrome P450–catalyzed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis

(2012) Sarah M Barry et al.   Nature Chemical Biology

Cine Substitution of Arenes Using the Aryl Carbamate as a Removable Directing Group

(2012) Tehetena Mesganaw et al.   ORGANIC LETTERS

Iridium-catalyzed C–H borylation of quinolines and unsymmetrical 1,2-disubstituted benzenes: insights into steric and electronic effects on selectivity

(2012) Hazmi Tajuddin et al.   Chemical Science

Ruthenium-catalyzed direct oxidative alkenylation of arenes through twofold C–H bond functionalization

(2012) Sergei I. Kozhushkov et al.   Chemical Science

Copper-Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights

(2011) Alison E. Wendlandt et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Carboxylate-Assisted Transition-Metal-Catalyzed C−H Bond Functionalizations: Mechanism and Scope

(2011) Lutz Ackermann   CHEMICAL REVIEWS

Guiding principles for site selective and stereoselective intermolecular C–H functionalization by donor/acceptor rhodium carbenes

(2011) Huw M. L. Davies et al.   CHEMICAL SOCIETY REVIEWS

Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

(2011) Ourida Saidi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C–H Bond Arylation

(2011) Bo Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Overturning Indolyne Regioselectivities and Synthesis of Indolactam V

(2011) Sarah M. Bronner et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Cope Rearrangement in the Reaction Catalyzed by Dimethylallyltryptophan Synthase?

(2011) Louis Y. P. Luk et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalysis for fluorination and trifluoromethylation

(2011) Takeru Furuya et al.   NATURE

Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines

(2011) Lutz Ackermann et al.   ORGANIC LETTERS

Directed Oxidative Cyclizations to C2- or C4-Positions of Indole: Efficient Construction of the Bicyclo[4.3.1]Decane Core of Welwitindolinones

(2011) Vikram Bhat et al.   ORGANIC LETTERS

Copper(II)-Catalyzed meta-Selective Direct Arylation of α-Aryl Carbonyl Compounds

(2010) Hung A. Duong et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Electronic effects in iridium C–H borylations: insights from unencumbered substrates and variation of boryl ligand substituents

(2010) Britt A. Vanchura et al.   CHEMICAL COMMUNICATIONS

Organocatalytic strategies for the asymmetric functionalization of indoles

(2010) Giuseppe Bartoli et al.   CHEMICAL SOCIETY REVIEWS

Enzymatic functionalization of carbon–hydrogen bonds

(2010) Jared C. Lewis et al.   CHEMICAL SOCIETY REVIEWS

Regioselective Oxidative Arylation of Indoles BearingN-Alkyl Protecting Groups: Dual C−H Functionalization via a Concerted Metalation−Deprotonation Mechanism

(2010) Shathaverdhan Potavathri et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Indolyne Experimental and Computational Studies: Synthetic Applications and Origins of Selectivities of Nucleophilic Additions

(2010) G-Yoon J. Im et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis of Phenanthrone Derivatives fromsec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C−H Bond Activation and Enolate Cyclization

(2010) Parthasarathy Gandeepan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through CH Bond Cleavage

(2009) Lutz Ackermann et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

(2009) Lutz Ackermann et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Diaryliodonium Salts: A Journey from Obscurity to Fame

(2009) Eleanor���A. Merritt et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Characterization ofcyclo-Acetoacetyl-l-Tryptophan Dimethylallyltransferase in Cyclopiazonic Acid Biosynthesis: Substrate Promiscuity and Site Directed Mutagenesis Studies

(2009) Xinyu Liu et al.   BIOCHEMISTRY

C−H Activation for the Construction of C−B Bonds

(2009) Ibraheem A. I. Mkhalid et al.   CHEMICAL REVIEWS

Concise Synthesis of the Bicyclic Scaffold ofN-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization

(2009) Xia Tian et al.   ORGANIC LETTERS

Indolynes as Electrophilic Indole Surrogates: Fundamental Reactivity and Synthetic Applications

(2009) Sarah M. Bronner et al.   ORGANIC LETTERS

A Meta-Selective Copper-Catalyzed C-H Bond Arylation

(2009) R. J. Phipps et al.   SCIENCE

Synthesis of Indolines and Tetrahydroisoquinolines from Arylethylamines by PdII-Catalyzed CH Activation Reactions

(2008) Jiao-Jie Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ergot Alkaloid Biosynthesis inAspergillus fumigatus

(2008) Ole Rigbers et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions

(2008) Robert J. Phipps et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Analysis of the Concerted Metalation-Deprotonation Mechanism in Palladium-Catalyzed Direct Arylation Across a Broad Range of Aromatic Substrates

(2008) Serge I. Gorelsky et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles

(2008) Shathaverdhan Potavathri et al.   TETRAHEDRON LETTERS