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Diarylmethylamines are key intermediates and products in the pharmaceutical industry. Herein we disclose a novel method toward the synthesis of these important compounds via C-H functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic C-H with in situ arylation by a NiXantPhos-based palladium catalyst (50-93 % yield, 29 examples). The method is also successful with N-Boc-tetrahydroisoquinolines. The advantages of this method are it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling. Skipping steps! Diarylmethylamines are key intermediates and products in the pharmaceutical industry. A novel method toward the synthesis of these important compounds via C-H functionalization is reported. A reversible deprotonation of N-Boc benzylalkylamines at the benzylic C-H is coupled with in situ arylation with a (NiXantPhos)Pd-based catalyst (50-93 % yield, 29 examples). The advantages of this method are that it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling.

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

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The condensation of 3,4-disubstituted phenylethylamine and benzaldehyde furnished 1-phenyl-6,7-disubstituted-1,2,3,4-tetrahydroisoquinolines 1 which on reaction with 1,3-dibromopropane gave 1-phenyl-6,7-disubstituted-2-(3-bromopropyl)-1,2,3,4-tetrahydroisoquinolines 2.The reaction of 2 with different secondary amines resulted in the synthesis of 3.The compounds 3 were screened for their in vitro antitubercular activity against Mycobacterium smegmatis, and some of them have been found to be total inhibitors of M.Smegmatis.

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Tetrahydroisoquinoline – Wikipedia,
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Chemical Research Letters, May 2021. 22990-19-8, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.22990-19-8, Name is 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N. In a Article,once mentioned of 22990-19-8

Sodium hydrogen telluride reduces imonium salts efficiently at room temperature in ethanol.The products of the reaction depend upon the pH.Under alkaline pH only dihydro-derivatives are formed.Under acid pH (6-7) the products depend on the structure of the salt.The tellurium can be recovered quantitatively.

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

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Hybrid catalyst systems to achieve acceptorless dehydrogenation of N-heterocycles and tetrahydronaphthalenes-model substrates for liquid organic hydrogen carriers-were developed. A binary hybrid catalysis comprising an acridinium photoredox catalyst and a Pd metal catalyst was effective for the dehydrogenation of N-heterocycles, whereas a ternary hybrid catalysis comprising an acridinium photoredox catalyst, a Pd metal catalyst, and a thiophosphoric imide organocatalyst achieved dehydrogenation of tetrahydronaphthalenes. These hybrid catalyst systems allowed for 2 molar equiv of H2 gas release from six-membered N-heterocycles and tetrahydronaphthalenes under mild conditions, i.e., visible light irradiation at rt. The combined use of two or three different catalyst types was essential for the catalytic activity.

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

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Reported is an achiral CpxRhIII/chiral carboxylic acid catalyzed asymmetric C?H alkylation of diarylmethanamines with a diazomalonate, followed by cyclization and decarboxylation to afford 1,4-dihydroisoquinolin-3(2H)-one. Secondary alkylamines as well as nonprotected primary alkylamines underwent the transformation with high enantioselectivities (up to 98.5:1.5 e.r.) by using a newly developed chiral carboxylic acid as the sole source of chirality to achieve enantioselective C?H cleavage by a concerted metalation-deprotonation mechanism.

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

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A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K3PO4·3H2O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K3PO4·3H2O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology.

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

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Only four types of dimeric precursors [RuCl2(eta6-arene)]2 for the synthesis of Noyori’s half sandwich diamine catalysts [RuCl(TsDPEN)(eta6-arene)] are commercially available, yet so far no study has tried to systematically evaluate how these systems perform during the asymmetric transfer hydrogenation of various 3,4-dihydroisoquinolines (i.e., the typical substrates for Noyori asymmetric transfer hydrogenation benchmarking). Experiments combined with molecular modeling allowed us to assess their properties and formulate a hypothesis clarifying the difference in enantioselectivity of these systems.

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Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-alkylquinoline-3-carbaldehydes as well as the corresponding 4-alkyl isomers and pyridine analogues. These processes involve dual C-H bond functionalization. Acetic acid is used as a cosolvent and acts as the sole promoter of these transformations.

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Chemical Research Letters, May 2021. Research speed reading in 2021. Related Products of 22990-19-8, The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 22990-19-8, Name is 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N. In a Article,once mentioned of 22990-19-8

A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothieno<2,3-c>pyridines, and related compounds were evaluated for their ability to inhibit binding of <(3)H>-1-<1-(2-thienyl)piperidine and <(3)H>-N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.

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

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Several 1-alkyl-1,2,3,4-tetrahydroisoquinoline (TIQ) derivatives, which may play a role in Parkinson’s disease, have been synthesized via Pummerer-type cyclization of the sulfonium ion formed in situ from N-formyl sulfoxide. Using an in vitro trypan blue exclusion assay, high concentrations of TIQ derivatives possessing bulky alkyl group substituents such as 1-cyclobutyl-, 1-cyclohexyl-, 1-phenyl- or 1-benzyl- at the C-1 position were found to significantly affect the viability of PC12 cells. Moreover, TIQ derivatives that moderately or strongly induced apoptosis (e.g., 1-phenyl-TIQ and 1-cyclohexyl-TIQ, respectively) paralleled the results obtained using the trypan blue exclusion assay. These results suggest that the size and electron-donating properties of functional groups may affect the cytotoxicity of TIQ derivatives.

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