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Chemical Research Letters, May 2021. Research speed reading in 2021. Electric Literature of 3340-78-1, The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 3340-78-1, Name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N. In a Article,once mentioned of 3340-78-1

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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A mild and metal-free DEAD-promoted (DEAD = diethyl azodicarboxylate) oxidative Ugi-type reaction of tertiary amines has been demonstrated. The reaction gives easy access to alpha-amino amides and imides with diverse functional groups in good isolated yields. This Ugi-type approach achieves an unprecedented synthesis of alpha-amino amide analogues with the assistance of dicarboxylic acids, and not water, for the introduction of the carbonyl oxygen atom of the amide moiety. Mechanistic studies indicated that the dicarboxylic acids may readily undergo an intramolecular annulation, instead of the Mumm rearrangement, to give the desired amide with one molecule of anhydride released.

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

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Two-dimensional covalent organic frameworks (2D-COFs) are excellent candidates for photocatalytic organic transformations due to their periodic columnar pi-arrays and ordered nanochannels. Here, we present a novel 2D-COF that features permanent porosity with high surface area and large pore volume, and exhibits a high crystallinity and an excellent stability. Indeed, the new 2D-COF was found to be a highly efficient, metal-free, recyclable heterogeneous photocatalyst for oxidative C-H functionalizations under visible-light irradiation using O2 as a green oxygen source.

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

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A rapid, transition metal-free, high-yielding, tetrabutylammonium bromide-promoted method of N-arylation is reported within. The optimized conditions tolerated a wide range of secondary amines and was equally effective with bromo- and chlorobenzene-including substituted aryl halides. The developed method is found to be effective for N-arylation when compared to earlier methods which involve harsh conditions, transition metals, lack of scalability, and long reaction times. Our method utilizes conventional heating only; it is readily scalable; and the products are facile to purify.

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

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A highly efficient metal-free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety of trialkylamines, pharmaceuticals, and alkaloids but remarkably also allows the lowest catalyst loading (0.00001 mol % or 0.1 ppm) ever reported for an organic dye. Bruylants reactions and C-alkylation/decyanations were performed on the obtained alpha-aminonitriles to demonstrate the postfunctionalization of complex molecules. The catalytic system is furthermore applied in the short and effective syntheses of the alkaloids (±)-crispine A and the tetraponerines T7 and T8.

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

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Herein, we describe a protocol for alkylation reactions of C(sp3)-H bonds with diacyl peroxides by means of a process involving cross-coupling between an alkyl radical and an alpha-Aminoalkyl radical. The mild, catalyst-And additive-free conditions make this protocol superior to previously reported C(sp3)-H alkylation strategies. The protocol was applied to 1,2,3,4-Tetrahydroisoquinolines and a tetrahydro-beta-carboline derivative and could be carried out on a gram scale, indicating its utility for the alkylation of late-stage synthetic intermediates.

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

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N-Alkyl- and N-arylsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonates 1 have been synthesized from the corresponding 3,4-dihydroisochinoliniumbromides 7 and triethylphosphite.The N-unsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonate 10 is available starting from the 1,2,3,4-tetrahydroisochinolin-1-phosphonic acid by esterification with triethylformate and splitting off the formyl group of the primarily formed N-formyl derivative 14. – N-Quarternated tetrahydroisochinolines 19 and the 1-phosphorylated derivatives 17, respectively react with triethylphosphite in an unexpected way by dealkylation and not by splitting off the isochinolinring. – By Horner-synthesis with 1 the 1-aralkylidene-isochinolines 23 are available in moderate yields.

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

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A novel stable radical cation triarylaminium salt able to induce aerobic oxidative alpha-C-H functionalization of tertiary amines in catalytic amounts has been developed. The reaction is performed in the absence of any other additives under mild conditions and only requires atmosphere air as a sustainable co-oxidant.

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

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This invention relates to a kind of used for visible light catalytic metal organic framework material and its synthetic method and application. The method comprises the following steps: the two organic ligand H 2 1 and H 2 2 in N, N-dimethyl formamide (DMF) solvent after uniformly mixing, adding ZrCl 4, in acetic acid under the control of the metal-organic framework material is obtained by reacting UIO-68Se, wherein the molar ratio of the two kinds of organic ligand 1:1-1:4. The material can be used as a visible-light responsive photocatalyst, the catalytic under the environment of air occurs and a nucleophilic reagent addition a cross-coupling reaction. The invention is based on the metal organic framework material having photocatalyst activity is high, the circulating is good, strong stability, easy separation and recycling, and the like. (by machine translation)

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

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An aerobic photocatalytic oxidative cyanation of tertiary amines providing valuable alpha-aminonitriles in good to excellent yields was developed. Mild reaction conditions and low catalyst loading are attractive features of the protocol. The Royal Society of Chemistry 2011.

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