3558-28-9

Usage

Type of compound

Derivative of indole

Indole

Heterocyclic compound found in plants

Physical state

Pale yellow solid

Uses

Precursor in the synthesis of various organic compounds

Applications

Pharmaceutical, dyes, pigments, plasticizers, antioxidants, and optical brighteners

Potential use

Organic electronic devices and fluorescent probe for detecting DNA damage

Safety precautions

Harmful if ingested or inhaled, causes skin and eye irritation

Upstream product

• 10257-92-8 2-phenyl-3-methyl-1H-indole 
• 854670-71-6 1-(N-methyl-anilino)-1-phenyl-acetone 
• 2739-12-0 N-methylaniline hydrochloride 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 93-89-0 benzoic acid ethyl ester 
• 1821-38-1 N-methyl-2-ethylphenylamine 
• 74825-94-8 (E)-N-methyl-N-(1-phenylprop-1-enyl)benzenamine 
• 59411-03-9 N-(2-Acetyl-phenyl)-N-methyl-benzamide 
• 83824-10-6 3-methyl-2-phenylindole-1-carboxaldehyde 
• 7647-01-0 hydrogenchloride 
• 869301-70-2 [2-((Z)-1-Benzenesulfonyl-2-phenyl-vinyl)-phenyl]-methyl-amine 

Downstream Products

• 75834-27-4 methoxy-6 dimethyl-1,3-phenyl-2 indol 
• 17182-60-4 N-methyl-2-phenylquinolin-4(1H)-one 
• 75834-26-3 Hydroxy-3 dimehyl-1,3-phenyl-2 indoline 
• 75834-31-0 hydroperoxy-3 indoline 
• 1446319-72-7 6,10b-dimethyl-2-nitro-5a-phenyl-5a,6,10b,11-tetrahydrochromeno[2,3-b]indole 
• 1446319-84-1 C₂₇H₂₉N₃O₃Si 

Relevant academic research and scientific papers

Chiral-Phosphoric-Acid-Catalyzed C6-Selective Pictet-Spengler Reactions for Construction of Polycyclic Indoles Containing Spiro Quaternary Stereocenters

Compared with the well-established asymmetric Pictet-Spengler reactions on the pyrrole ring of indoles, the catalytic asymmetric Pictet-Spengler reaction on the benzene ring of indoles has been rarely studied. Herein the C6-selective Pictet-Spengler react

Direct C-H bond activation: Palladium-on-carbon as a reusable heterogeneous catalyst for C-2 arylation of indoles with arylboronic acids

Direct C(sp2)-H bond functionalization of indoles with arylboronic acids is achieved using palladium supported on carbon as a reusable heterogeneous catalyst in the presence of an oxidant under mild conditions. The current protocol formed exclusive C-2 selective products without the aid of any ligand or directing group. The catalyst is reusable for up to four catalytic cycles with the retention of catalytic efficiency.

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

The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C-H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade.

Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans

An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.

Mild and selective base-free C-H arylation of heteroarenes: experiment and computation

A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck-Matsuda type coupling mechanism.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles

A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.

Rhodium-catalyzed annulation of tertiary aniline N-oxides to N-alkylindoles: Regioselective C-H activation, oxygen-atom transfer, and N-dealkylative cyclization

[Cp?RhIII]-catalyzed annulation of tertiary aniline N-oxides with alkynes was reported to achieve the challenging ortho C-H functionalization of tertiary anilines via N-O bond acting as a traceless directing group. More significantly, this system represents the first example which integrates C-H activation, oxygen-atom transfer, and N-dealkylative cyclization in one reaction. This unprecedented coupling reaction has allowed the construction of N-alkylindole derivatives in high efficiency with broad substrate scope and good functional group tolerance.

Rh(III)-catalyzed chemoselective C-H functionalizations of tertiary aniline: N -oxides with alkynes

In this work, we report novel Rh(iii)-catalyzed chemoselective functionalizations of tertiary aniline N-oxides with alkynes, including annulation via the sequential C(sp2)-H and C(sp3)-N activation for the formation of N-alkylindoles and an O-atom transfer (OAT) process for the synthesis of acetophenones.