36710-74-4

Upstream product

• 19493-44-8 1-chloroisoquinoline 
• 1532-72-5 isoquinoline N-oxide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 19658-77-6 1-iodoisoquiniline 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 14774-77-7 p-methoxyphenyllithium 
• 119-65-3 isoquinoline 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 104-94-9 4-methoxy-aniline 
• 1262841-97-3 C₂₃H₂₃NO₃S 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 1448157-21-8 1-(4-(4-methylpiperazin-1-yl)phenyl)isoquinoline 
• 1443308-98-2 C₂₇H₂₆NO₃⁽¹⁺⁾*Br^(1-) 
• 1443308-92-6 C₂₃H₂₀NO⁽¹⁺⁾*Br^(1-) 

Relevant academic research and scientific papers

Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents

A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.

Electrogenerated Chemiluminescent Chemodosimeter Based on a Cyclometalated Iridium(III) Complex for Sensitive Detection of Thiophenol

Thiophenol is the simplest aromatic thiol that is utilized for various applications in industry and agriculture. However, it should be used with care because thiophenol is readily absorbed into the human body by inhalation and ingestion, which leads to serious internal injuries. Thus, there is an urgent need for real-time and accurate monitoring of thiophenol. Despite remarkable advantages of electrogenerated chemiluminescence (ECL) analysis, ECL thiophenol probes have never been reported. Herein, a new strategy for the rapid detection of thiophenol by use of an ECL turn-on chemodosimeter based on a cyclometalated Ir(III) complex is described. This analytical system showed superior sensitivity [limit of detection (LOD) value, 3.8 nM] in comparison to the conventional fluorescence method. In addition, our system exhibited remarkable selectivity and reaction rate toward thiophenol over other analytes. Moreover, it was successfully applied to quantify thiophenol in real water samples, providing a new proof-of-concept for field monitoring based on ECL.

Phase-selective modulation of TiO2 for visible light-driven C–H arylation: Tuning of absorption and adsorptivity

To understand and modify TiO2 for organic photoreaction, two points are important: improving light absorption and retaining adsorption sites for organic reagents. Herein, we tuning the absorption and adsorption of TiO2 by introducing

Method for solvent accelerated selective dehydrogenation of tetrahydroisoquinoline type compound

The invention discloses a method for synthesizing 1-substituted-3,4-dihydroisoquinoline through the solvent accelerated selective partial dehydrogenation of a 1-substituted-1,2,3,4-tetrahydroisoquinoline compound. For a simple and easily obtained cyclic amine type compound such as a tetrahydroisoquinoline compound, a corresponding imine compound can be obtained through selective dehydrogenation; the conversion ratio of the cyclic amine type compound is higher; further, the proportion of a partially dehydrogenated product to a fully dehydrogenated product is more than 20 to 1. The method is simple and convenient to operate, is practical, easy and feasible, and is mild in reaction condition; the actual cost is greatly reduced. In addition, a method for synthesizing 3,4-dihydroisoquinoline through the direct dehydrogenation of tetrahydroisoquinoline has the advantages of atom economy and environmental friendliness.

Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids

The first palladium-catalyzed decarbonylative coupling of phenyl 2-azinecarboxylates and arylboronic acids is presented. The key for the development of this decarbonylative coupling is the use of Pd/dcype as a catalyst. A wide range of 2-azinecarboxylates can undergo the present coupling reaction to afford 2-arylazines. By combination with previously reported nickel-catalyzed decarbonylative coupling, we achieved a chemoselective sequential decarbonylative coupling of pyridine dicarboxylate to synthesize 2,4-diarylpyridine.

Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides

Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.

Enhancing effects of salt formation on catalytic activity and enantioselectivity for asymmetric hydrogenation of isoquinolinium salts by dinuclear halide-bridged iridium complexes bearing chiral diphosphine ligands

Asymmetric hydrogenation of 1- and 3-substituted and 1,3-disubstituted isoquinolinium chlorides using triply halide-bridged dinuclear iridium complexes [{Ir(H)(diphosphine)} 2(μ -Cl)3]Cl has been achieved by the strategy of HCl salt formation of isoquinolines to afford the corresponding chiral 1,2,3,4-tetrahydroisoquinolines (THIQs) in high yields and with excellent enantioselectivities after simple basic workup. The effects of salt formation have been investigated by time-course experiments, which revealed that the generation of isoquinolinium chlorides clearly prevented formation of the catalytically inactive dinuclear trihydride complex, which was readily generated in the catalytic reduction of salt-free isoquinoline substrates. Based on mechanistic investigations, including by 1H and 31P{1H} NMR studies and the isolation and characterization of several intermediates, the function of the chloride anion of the isoquinolinium chlorides has been elucidated, allowing us to propose a new outer-sphere mechanism involving coordination of the chloride anion of the substrates to an iridium dihydride species along with a hydrogen bond between the chloride ligand and the N-H proton of the substrate salt.

Organic fluorescent thermometers based on borylated arylisoquinoline dyes

Borylated arylisoquinolines with redshifted internal charge-transfer (ICT) emission were prepared and characterized. Upon heating, significant fluorescence quenching was observed, which forms the basis for a molecular thermometer. In the investigated temp

Total syntheses of menisporphine and daurioxoisoporphine c enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium Salt

Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.

Preparation and pH-switching of fluorescent borylated arylisoquinolines for multilevel molecular logic

The preparation of pH-switchable fluorescent borylated arylisoquinoline dyes via a flexible iridium-catalyzed route is reported. The obtained dyes feature aromatic amino substitution and lateral aliphatic amino groups as electron donors. The photophysical