78317-82-5

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 106-38-7 para-bromotoluene 
• 67-56-1 methanol 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 493-05-0 isochromane 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 106-49-0 p-toluidine 
• 106-44-5 p-cresol 
• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 135-19-3 β-naphthol 
• 119-65-3 isoquinoline 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1189050-53-0 1-(1-nitroethyl)-2-(4-methyl)phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1189050-60-9 2-(4-methyl)phenyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 1132765-75-3 1-(nitromethyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 
• 1276118-45-6 1-(2-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one 
• 1380208-84-3 4-hydroxy-6-methyl-3-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-2H-chromen-2-one 
• 1380208-71-8 C₂₂H₂₇NO 
• 1380166-39-1 2-(p-tolyl)1-[((4-pentylphenyl)ethynyl)]-1,2,3,4-tetrahydroisoquinoline 
• 1380166-34-6 2-(p-tolyl)-1-[(phenylethynyl)]-1,2,3,4-tetrahydroisoquinoline 
• 1374694-55-9 (S)-1-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-1-one 
• 41852-28-2 N-p-Tolyl-3,4-dihydro-isochinoliniumbromid 
• 1423058-40-5 4-hydroxy-3-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-2H-chromen-2-one 
• 1423058-43-8 1-(4-methylphenyl)-2-dimethylphosphonate-1,2,3,4-tetrahydroisoquinoline 
• 1428660-46-1 4-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-one 
• 1428660-52-9 1-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)pentan-3-one 

Relevant academic research and scientific papers

Photocatalyst- And transition-metal-free α-allylation of: N -aryl tetrahydroisoquinolines mediated by visible light

A convenient and efficient α-allylation of N-aryl tetrahydroisoquinolines has been achieved. This transformation can be realized under only visible light irradiation without the aid of transition metals or photocatalysts. The mechanism involves a novel in situ-generated electron-donor-acceptor (EDA) complex between the N-aryl tetrahydroisoquinolines and an allyl or a benzyl bromide. Irradiation with purple light triggered single-electron transfer (SET) from the N-aryl tetrahydroisoquinolines to the allyl or benzyl bromide of the EDA complex, inducing the formation of the corresponding allyl or benzyl radical and the subsequent radical-radical coupling. This approach represents the first example of a photocatalyst- and transition-metal-free α-allylic and benzylic functionalization of N-aryl tetrahydroisoquinolines.

Direct Near Infrared Light–Activatable Phthalocyanine Catalysts

The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa

Catalytic Amination of Phenols with Amines

Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

An oxidant- And catalyst-free electrooxidative cross-coupling approach to 3-tetrahydroisoquinoline substituted coumarins

A direct electrooxidative cross-dehydrogenative-coupling (CDC) reaction betweenN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins has been realized. This protocol provides a green, mild and fast method to construct 3-tetrahydroisoquinoline substituted coumarins in the absence of any catalysts and exogenous oxidants. A variety ofN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins are compatible with this transformation to give the corresponding products in moderate to excellent yields. Moreover, the results of control experiments, cyclic voltammetry experiments, and density functional theory (DFT) calculations indicated that the electrooxidative CDC reaction might involve both radical addition and nucleophilic addition processes.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Visible-light induced Cross-Dehydrogenative-Coupling (CDC) reactions of N-aryl tetrahydroisoquinolines under aerobic conditions

A visible-light induced cross-dehydrogenative-coupling (CDC) reaction of N-aryl tetrahydroisoquinolines was developed under mild aerobic conditions. This protocol proceeded smoothly with a large range of nucleophiles (nitroalkane, dimethyl phosphite, dimethyl malonate, N-methyl indole, TMSCN) under metal-free conditions and an oxygen atmosphere, forming a new C–C bond. Visible-light played a significant acceleration effect in this reaction.

Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: A New Synthetic Approach to α-Monofluoromethyl Tertiary Amines

A cross dehydrogenative coupling reaction of tetrahydroisoquinolines with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide had been developed. CuBr/TBHP was identified as the best catalyst and oxidant. A variety of coupling products were obtained with good t

Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).

Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions

Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici