78317-78-9

Upstream product

• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 106-47-8 4-chloro-aniline 
• 493-05-0 isochromane 
• 106-39-8 bromochlorobenzene 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 13519-75-0 N-ethyl-4-chloro-aniline 
• 102912-87-8 [1-(2-Bromo-phenyl)-meth-(E)-ylidene]-(4-chloro-phenyl)-amine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 356531-18-5 N-(2-bromobenzyl)-4-chloroaniline 
• 104-94-9 4-methoxy-aniline 
• 637-87-6 1-Chloro-4-iodobenzene 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1276118-48-9 1-(2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one 
• 1380166-36-8 2-[(4-chlorophenyl)-1-(phenylethynyl)]-1,2,3,4-tetrahydroisoquinoline 
• 1382465-07-7 (2‐(4‐chlorophenyl)‐1,2,3,4‐tetrahydroisoquinolin‐1‐yl)diphenylphosphine oxide 
• 1580003-22-0 C₁₈H₁₆ClNO 
• 1616792-13-2 2-(2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-2,2-difluoro-1-phenylethanone 
• 1419612-79-5 1-(1H-indol-3-yl)-2-(4-chloro-phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp3 C-H bonds with molecular oxygen

A ligand-free iron-catalyzed method for the oxygenation of benzylic sp3 C-H bonds by molecular oxygen (1 atm) using a thiyl radical as a cocatalyst has been developed. This transformation provides a facile access to amides, esters and ketones from readily accessible corresponding amines, ethers and alkanes. It features high regioselectivity, mild oxidative conditions and excellent functional group compatibility, providing good opportunities to the site-selective functionalization of complex molecules. Preliminary mechanistic studies suggest that this reaction may not undergo a benzylic cation intermediate pathway and the carbonyl oxygen atom in the products may be derived from molecular oxygen.

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

A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence

N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.

N-Phenyl-1,2,3,4-tetrahydroisoquinoline: An Alternative Scaffold for the Design of 17β-Hydroxysteroid Dehydrogenase 1 Inhibitors

17β-Hydroxysteroid dehydrogenases catalyse interconversion at the C17 position between oxidized and reduced forms of steroidal nuclear receptor ligands. The type 1 enzyme, expressed in malignant cells, catalyses reduction of the less-active estrone to estradiol, and inhibitors have therapeutic potential in estrogen-dependent diseases such as breast and ovarian cancers and in endometriosis. Synthetic decoration of the nonsteroidal N-phenyl-1,2,3,4-tetrahydroisoquinoline (THIQ) template was pursued by using Pomeranz-Fritsch-Bobbitt, Pictet-Spengler and Bischler-Napieralski approaches to explore the viability of this scaffold as a steroid mimic. Derivatives were evaluated biologically in vitro as type 1 enzyme inhibitors in a bacterial cell homogenate as source of recombinant protein. Structure-activity relationships are discussed. THIQs possessing a 6-hydroxy group, lipophilic substitutions at the 1- or 4-positions in combination with N-4′-chlorophenyl substitution were most favourable for activity. Of these, one compound had an IC50 of ca. 350 nM as a racemate, testifying to the applicability of this novel approach.

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

Electrocatalytic C(sp3)-H/C(sp)-H cross-coupling in continuous flow through TEMPO/copper relay catalysis

Electrocatalytic dehydrogenative C(sp3)-H/C(sp)-H cross-coupling of tetrahydroisoquinolines with terminal alkynes has been achieved in a continuous-flow microreactor through 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/copper relay catalysis. The reaction

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.

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