136672-24-7

Upstream product

• 6965-44-2 N-Methyl-indole-3-carbinol 
• 19012-03-4 N-methyl-3-formylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 5720-07-0 4-methoxyphenylboronic acid 
• 875-30-9 1,3-dimethylindole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 824-21-5 N-methylindoline 
• 105-13-5 4-Methoxybenzyl alcohol 
• 603-76-9 1-methylindole 
• 698-02-2 N,N-dimethyl-o-iodoaniline 
• 62167-04-8 2-((4-methoxyphenyl)ethynyl)-N,N-dimethylaniline 
• 19260-05-0 1-methylgramine methiodide 

Relevant academic research and scientific papers

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines

Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.

Benzylic C(sp3)-C(sp2) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis

A mechanistically unique functionalization strategy for a benzylic C(sp3)-H bond has been developed based on the facile oxidation event of indole substrates. This novel pathway was initiated by efficient radical generation at the benzylic position of the substrate, with subsequent transition metal catalysis to complete the overall transformation. Ultimately, an aryl or an acyl group could be effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, respectively. The developed method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies have shown that competitive hydrogen atom transfer (HAT) processes, which are frequently encountered in conventional methods, are not involved in the product formation process of the developed strategy.

Efficient N-heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids

Pyridine-bridged bis-benzimidazolylidene nickel complexes exhibited very high catalytic activity toward cross coupling of inactive (hetero)aryl benzylic ammonium salts with (hetero)aryl and alkenyl boronic acids under mild reaction conditions. Even at 2 mol% catalyst loading, a wide range of substrates for both coupling partners with different steric and electronic properties were well tolerated.

Catalytic Tandem and One-Pot Dehydrogenation-Alkylation and -Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes

The ruthenium-hydride catalyst has been successfully used for the tandem sp3 C-H dehydrogenation-alkylation reaction of saturated hydrocarbon substrates with alcohols to form the alkyl-substituted alkene and arene products. The analogous one-pot dehydrogenation-insertion of saturated ketones with alkenes and dienes directly yielded synthetically useful 2-alkylphenol and benzopyran products in a highly regio- and stereoselective manner without forming any wasteful byproducts. (Chemical Equation Presented).

Solvent-free Br?nsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Br?nsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.

Dearomative indole (3 + 2) cycloaddition reactions

A diastereoselective (3 + 2) dearomative annulation of 3-substituted indoles with α-haloketones has been developed. Significant regiochemical control was observed. This methodology provides easy access to highly functionalized cyclopenta- or cyclohexa-fused indoline compounds, which are common structures of many natural products. The synthetic potential of this reaction was demonstrated in the concise syntheses of the core structures of vincorine, isocorymine, and aspidophylline A. DFT studies (B3LYP-D3/6- 311++G**/MeOH) on cyclization mechanisms involving the 2-hydroxyallyl cation and its deprotonated oxyallyl cation have been performed. Under the reaction conditions, with a sparingly soluble Na2CO 3 base, both species may be present and both pathways are viable. Both pathways support the formation of the experimentally observed O-bound intermediate, its transformation to the final product, the regiochemical and eventual stereochemical outcome of the kinetic cyclization product, and the thermodynamic preference for formation of the final stereoisomer.

Au(III)/TPPMS-catalyzed benzylation of indoles with benzylic alcohols in water

A novel and efficient method for the Au(III)/TPPMS-catalyzed direct substitution reaction of benzhydryl and benzylic alcohols with indoles in water is developed. Au(III)/TPPMS is an effective catalyst for the benzylation of the strong π nucleophile 1-methylindole, while common Bronsted or Lewis acids are ineffective.