Recent Advances in Indole Synthesis and the Related Alkylation

A Metal-Free Reductive N-Alkylation of Indoles with Aldehydes

(2021) Nicholas A. Clanton et al.   ORGANIC LETTERS

Domino C–N Bond Formation via a Palladacycle with Diaziridinone. An Approach to Indolo[3,2-b]indoles

(2021) Sudarshan Debnath et al.   ORGANIC LETTERS

Diastereoselective Synthesis of Dihydro-quinolin-4-ones by a Borane-Catalyzed Redox-Neutral endo-1,7-Hydride Shift

(2021) Garrit Wicker et al.   ORGANIC LETTERS

Electrocatalytic Dehydrogenative Cyclization of 2-Vinylanilides for the Synthesis of Indoles

(2021) Yun-Tao Zheng et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of Dipeptide, Amide, and Ester without Racemization by Oxalyl Chloride and Catalytic Triphenylphosphine Oxide

(2021) Ji-Wei Ren et al.   ORGANIC LETTERS

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles

(2021) Xu Yan et al.   ORGANIC LETTERS

Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides

(2020) Shuo Yuan et al.   ORGANIC LETTERS

B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

(2020) Shyam Basak et al.   ACS Catalysis

Enantioselective Catalytic Synthesis of N-alkylated Indoles

(2020) Dmitri Trubitsõn et al.   Symmetry-Basel

Nickel-Catalyzed Mizoroki–Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles

(2020) Xu Chen et al.   ORGANIC LETTERS

Rhodium‐Catalyzed Chemodivergent Regio‐ and Enantioselective Allylic Alkylation of Indoles

(2020) Minghe Sun et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis of N-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction

(2019) Zhan Dong et al.   ORGANIC LETTERS

CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence

(2019) Yuxuan Ye et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

One-Pot Synthesis of N-Imidoyl-(1H)-Indoles via Palladium-Catalyzed Oxidative Insertion Domino Reaction with Isocyanide and Arylboronic Acid

(2019) Shou-wei Tao et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction

(2019) Jamie R. Allen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

(2019) Weishuang Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Rhenium-Catalyzed Intramolecular Carboalkoxylation and Carboamination of Alkynes for the Synthesis of C3-Substituted Benzofurans and Indoles

(2019) Ming-Guang Rong et al.   ORGANIC LETTERS

Chemoselective N-Alkylation of Indoles in Aqueous Microdroplets

(2019) Elumalai Gnanamani et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Brønsted Acids Enable Three Molecular Rearrangements of One 3-Alkylidene-2H-1,2-oxazine Molecule into Distinct Heterocyles

(2018) Bhanudas Dattatray Mokar et al.   ORGANIC LETTERS

Metal and acid-free visible light-mediated Friedel-Crafts alkylation reactions of indole with anilines

(2018) Xiao-Qiang Dai et al.   TETRAHEDRON LETTERS

“Back-to-Front” Indole Synthesis Using Silver(I) Catalysis: Unexpected C-3 Pyrrole Activation Mode Supported by DFT

(2018) Aimee K. Clarke et al.   ACS Catalysis

Chiral phosphoric acid catalyzed enantioselective N-alkylation of indoles with in situ generated cyclic N-acyl ketimines

(2018) Lvye Zhang et al.   CHEMICAL COMMUNICATIONS

Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to p-quinone methides: efficient access to unsymmetrical diarylindolylmethanes

(2018) Raveendra Jillella et al.   NEW JOURNAL OF CHEMISTRY

Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid

(2018) Yue Cai et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer

(2018) Torsten Irrgang et al.   CHEMICAL REVIEWS

Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen

(2017) Giovanni Di Gregorio et al.   JOURNAL OF ORGANIC CHEMISTRY

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation

(2017) Pedro Juan Llabres-Campaner et al.   JOURNAL OF ORGANIC CHEMISTRY

Recent progress in transition-metal-catalyzed enantioselective indole functionalizations

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

Dual visible-light photoredox and palladium(ii) catalysis for dehydrogenative C2-acylation of indoles at room temperature

(2017) Manash Kumar Manna et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles

(2017) Kang Yuan et al.   ORGANIC LETTERS

Gold/Copper-Co-catalyzed Tandem Reactions of 2-Alkynylanilines: A Synthetic Strategy for the C2-Quaternary Indolin-3-ones

(2017) Yi-Jin Li et al.   ORGANIC LETTERS

Cs 2 CO 3 -catalyzed alkylation of indoles with trifluoromethyl ketones

(2017) Xiao-Dong Liu et al.   TETRAHEDRON

Friedel-Crafts Reaction of Indoles with Isatin-Derived β,γ-Unsaturated α-Keto Esters Using a BINOL-Derived Bisoxazoline (BOX)/Copper(II) Complex as Catalyst

(2016) Nai-Kai Li et al.   ADVANCED SYNTHESIS & CATALYSIS

Decarboxylative/decarbonylative C3-acylation of indoles via photocatalysis: a simple and efficient route to 3-acylindoles

(2016) Qing Shi et al.   GREEN CHEMISTRY

Construction of 9H-Pyrrolo[1,2-a]indoles by a Copper-Catalyzed Friedel–Crafts Alkylation/Annulation Cascade Reaction

(2016) Yongqing Sun et al.   JOURNAL OF ORGANIC CHEMISTRY

Ag(I)-Catalyzed Domino Cyclization–Addition Sequence with Simultaneous Carbonyl and Alkyne Activation as a Route to 2,2′-Disubstituted Bisindolylarylmethanes

(2016) Swastik Karmakar et al.   ORGANIC LETTERS

Lewis Acid-Catalyzed or Base-Promoted Regioselective Cycloisomerization ofN-Imidoyl-o-alkynylanilines for Synthesis ofN-Imidoyl-(1 H)-indoles and 4-Alkylidene-3,4-dihydroquinazolines

(2015) Takashi Otani et al.   ADVANCED SYNTHESIS & CATALYSIS

Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis

(2015) Xiaobei Chen et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis of N-vinylindoles through copper catalyzed cyclization reaction of N-(2-alkynylphenyl)imine

(2015) Zhi-Qiang Wang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Regio- and Enantioselective Synthesis ofN-Allylindoles by Iridium-Catalyzed Allylic Amination/Transition-Metal-Catalyzed Cyclization Reactions

(2014) Ke-Yin Ye et al.   CHEMISTRY-A EUROPEAN JOURNAL

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals

(2014) Edon Vitaku et al.   JOURNAL OF MEDICINAL CHEMISTRY

Pd(ii)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole-3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones

(2014) Rong Shen et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Copper-catalyzed decarboxylative C3-acylation of free (N–H) indoles with α-oxocarboxylic acids

(2014) Cuiping Wang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Brønsted Acid Catalyzed Cascade Reactions of 2-[(2-Aminophenyl)ethynyl]phenylamine Derivatives with Aldehydes: A New Approach to the Synthesis of 2,2′-Disubstituted 1H,1′H-3,3′-Biindoles

(2014) Antonio Arcadi et al.   ORGANIC LETTERS

[Cp∗IrCl2]2-catalysed cyclization of 2-alkynylanilines into indoles

(2014) Elumalai Kumaran et al.   TETRAHEDRON LETTERS

Choline chloride based eutectic solvents: direct C-3 alkenylation/alkylation of indoles with 1,3-dicarbonyl compounds

(2014) Anita Kailas Sanap et al.   RSC Advances

Cycloisomerization of 2-Alkynylanilines to Indoles Catalyzed by Carbon-Supported Gold Nanoparticles and Subsequent Homocoupling to 3,3′-Biindoles

(2013) Jesus E. Perea-Buceta et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols

(2013) Anggi Eka Putra et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina

(2013) Qiu Yu Lai et al.   NEW JOURNAL OF CHEMISTRY

Synthesis of indoles with a polyfluorinated benzene ring

(2013) Larisa V. Politanskaya et al.   TETRAHEDRON

In(OTf)3 catalyzed C3-benzylation of indoles with benzyl alcohols in water

(2013) Lin Wu et al.   RSC Advances

N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis

(2013) Yan-Chao Shi et al.   Organic Chemistry Frontiers

Cesium Carbonate-Promoted Hydroamidation of Alkynes: Enamides, Indoles and the Effect of Iron(III) Chloride

(2012) María Teresa Herrero et al.   ADVANCED SYNTHESIS & CATALYSIS

AsymmetricN-Allylation of Indoles Through the Iridium-Catalyzed Allylic Alkylation/Oxidation of Indolines

(2012) Wen-Bo Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Indoles in Multicomponent Processes (MCPs)

(2012) Morteza Shiri   CHEMICAL REVIEWS

New strategies for the synthesis of N-alkylated indoles (Review)

(2012) A. V. Karchava et al.   Chemistry of Heterocyclic Compounds

Domino Sonogashira Coupling/Cyclization Reaction Catalyzed by Copper and ppb Levels of Palladium: A Concise Route to Indoles and Benzo[b]furans

(2011) Ruiping Wang et al.   ADVANCED SYNTHESIS & CATALYSIS

Efficient and convenient C-3 functionalization of indoles through Ce(OAc)3/TBHP-mediated oxidative C–H bond activation in the presence of β-cyclodextrin

(2011) Yu Lin Hu et al.   GREEN CHEMISTRY

ZrCl4-Mediated Regio- and Chemoselective Friedel–Crafts Acylation of Indole

(2011) Sankar K. Guchhait et al.   JOURNAL OF ORGANIC CHEMISTRY

Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides

(2011) Benjamin J. Stokes et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation

(2011) Lei Jiao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ruthenium/TFA-catalyzed regioselective C-3-alkylation of indoles with terminal alkynes in water: efficient and unprecedented access to 3-(1-methylalkyl)-1H-indoles

(2010) Victorio Cadierno et al.   CHEMICAL COMMUNICATIONS

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

(2010) Anna J. Kochanowska-Karamyan et al.   CHEMICAL REVIEWS

Asymmetric Phase-Transfer-Catalyzed Intramolecular N-Alkylation of Indoles and Pyrroles: A Combined Experimental and Theoretical Investigation

(2010) Marco Bandini et al.   CHEMISTRY-A EUROPEAN JOURNAL

Chiral Brønsted acid catalyzed asymmetric Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives

(2010) Tsubasa Sakamoto et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Copper-Catalyzed CC Bond Formation through CH Functionalization: Synthesis of Multisubstituted Indoles fromN-Aryl Enaminones

(2009) Roberta Bernini et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Asymmetric Organocatalytic N-Alkylation of Indole-2-carbaldehydes with α,β-Unsaturated Aldehydes: One-Pot Synthesis of Chiral Pyrrolo[1,2-a]indole-2-carbaldehydes

(2009) Liang Hong et al.   CHEMISTRY-A EUROPEAN JOURNAL

Efficient Regioselective Synthesis of IndoleN-Carboximidamides andN-Carboximidoates by a Sequential Aza-Wittig/Ag(I)-Catalyzed Cyclization

(2009) Nian-Yu Huang et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereoselective Double Friedel−Crafts Alkylation of Indoles with Divinyl Ketones

(2009) Andrew C. Silvanus et al.   ORGANIC LETTERS

3-Aroylindoles via Copper-Catalyzed Cyclization of N-(2-Iodoaryl)enaminones

(2009) Sandro Cacchi et al.   SYNLETT

First example of FeCl3-catalyzed alkylation of indoles with pinenes

(2009) J.S. Yadav et al.   TETRAHEDRON LETTERS

Catalytic Synthesis of Indoles from Alkynes

(2008) Karolin Krüger (née Alex) et al.   ADVANCED SYNTHESIS & CATALYSIS

InBr3-Promoted Divergent Approach to Polysubstituted Indoles and Quinolines from 2-Ethynylanilines: Switch from an Intramolecular Cyclization to an Intermolecular Dimerization by a Type of Terminal Substituent Group

(2008) Norio Sakai et al.   JOURNAL OF ORGANIC CHEMISTRY

One-Pot Multicomponent Synthesis of Indoles from 2-Iodobenzoic Acid

(2007) Olivier Leogane et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

FeCl3-catalyzed alkylation of indoles with 1,3-dicarbonyl compounds: an expedient synthesis of 3-substituted indoles

(2007) J.S. Yadav et al.   TETRAHEDRON LETTERS