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An efficient method for an iron catalyzed oxidative indolation and methoxyphenylation of N-protected tetrahydroisoquinolines and isochroman is described including subsequent facile deprotection. The Royal Society of Chemistry 2010.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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We herein report a versatile and environmentally friendly electrochemical oxidative C-H phosphonylation protocol. This protocol features a broad substrate scope; not only C(sp2)-H phosphonylation, but also C(sp3)-H phosphonylation is tolerated well under exogenous-oxidant-free and metal catalyst-free electrochemical oxidation conditions.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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An efficient and high yield process for sp3 C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines is disclosed. This involves a visible light mediated photoredox Ugi-type reaction with carboxylic acids and isonitriles under aerobic conditions, employing Ru(bpy)3Cl2 as a photoredox catalyst and CH3CN as the solvent. CH3CN was found to be crucial for the process, and good to excellent yields were achieved for a wide variety of N-aryl-1,2,3,4-tetrahydroisoquinolines, carboxylic acids, and isonitriles. The developed methodology is attractive for the synthesis of a library of 1,2,3,4-tetrahydroisoquinolines. This journal is

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 3340-78-1, name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. Computed Properties of C15H15N

An aerobic oxidative cross-dehydrogenative coupling reaction between sp3 C-H and sp2 C-H bonds is developed by employing a vanadium catalyst (10 mol%) in an aqueous medium using molecular oxygen as the oxidant. This environmentally benign strategy exhibits larger substrate scope and shows high regioselectivity.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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The first report on heterogeneously catalyzed oxidative cyanation of various tertiary amines to the corresponding a-amino nitriles with high yields and selectivity by using hydrogen peroxide oxidant in presence of sodium cyanide and Fe(II) phthalocyanine supported on a polymer as catalyst is described. The present method has the added benefits of facile recovery of the catalyst from the reaction mixture and its subsequent use without further activation. Consistent catalytic activity with no metal leaching was observed during this course.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Reconfigurable system for automated optimization of diverse chemical reactions

Chemical synthesis generally requires labor-intensive, sometimes tedious trial-and-error optimization of reaction conditions. Here, we describe a plug-and-play, continuous-flow chemical synthesis system that mitigates this challenge with an integrated combination of hardware, software, and analytics. The system software controls the user-selected reagents and unit operations (reactors and separators), processes reaction analytics (high-performance liquid chromatography, mass spectrometry, vibrational spectroscopy), and conducts automated optimizations. The capabilities of this system are demonstrated in high-yielding implementations of C-C and C-N cross-coupling, olefination, reductive amination, nucleophilic aromatic substitution (SNAr), photoredox catalysis, and a multistep sequence. The graphical user interface enables users to initiate optimizations, monitor progress remotely, and analyze results. Subsequent users of an optimized procedure need only download an electronic file, comparable to a smartphone application, to implement the protocol on their own apparatus.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Electrochemical Cross-Dehydrogenative Coupling of N-Aryl-tetrahydroisoquinolines with Phosphites and Indole

A metal- and reagent-free, electrochemical cross-dehydrogenative coupling reaction of N-aryl-tetrahydroisoquinolines with phosphites and indole is developed. This method provides an environmentally benign and simple approach for the construction of C?P and C?C bonds in moderate to high yields with wide tolerance of functional groups.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Synthesis Of Biologically Active Bis(Indolyl)Methane Derivatives by Bisindole Alkylation of Tetrahydroisoquinolines with Visible-Light Induced Ring-Opening Fragmentation

A visible-light photoredox catalyzed ring-opening functionalization of tetrahydroisoquinolines with bisindole alkylation has been developed, which expedites a new vista for the synthesis of bis(indolyl)methane derivatives. The transformation comprises a series of cascade reactions, photoredox catalysis, amine oxidation, fragmentation and Friedel?Craft alkylation. Five of the prepared bis(indolyl)methane derivatives containing the para substitution group on the side chain of benzene suppressed cancer cell growth in human breast adenocarcinoma MDA-MB-231 cells, and one candidate demonstrated a significant effect on cell migration.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3)?H Bonds with Aryl Fluorides

A controllable mono- and di-multifluoroarylation of acyclic and cyclic N-aryl amines with aryl fluorides by photocatalyzed dual C(sp3)?H/C(sp2)?F functionalization has been developed, providing new access to a wide array of valuable alpha-fluoroarylated amines. In addition, the one-pot consecutive hetero-di-multifluoroarylation of N-aryl pyrrolidines and N,N-dimethylanilines was achieved with high to excellent diastereoselectivity. This new defluorinative C(sp3)?C(sp2) coupling is distinguished by a broad scope, good regioselectivity, and mild conditions as well as gram-scale and late-stage applicability, and thus constitutes a significant advance in the arylation of unactivated C(sp3)?H bonds with aryl fluorides.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline

Abstract: Alkynylation reactions of N-protected tetrahydroisoquinolines have been performed using several different protocols of cross dehydrogenative coupling. Initially, a CuCl-catalyzed method was investigated, which worked well with three different N-protecting groups, namely phenyl, PMP, and benzyl and t-BuOOH as oxidant in acetonitrile as solvent. The peroxide could then be replaced by simple air and acetonitrile for water, leading to an overall very environmentally friendly protocol. Finally, a decarboxylative alkynylation protocol starting from alkynoic acids was also developed using again air as oxidant. This avoids the use of gaseous alkynes in the introduction of short-chained alkyne substituents. Graphical abstract: [Figure not available: see fulltext.]

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem