Discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.

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

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2-(substituted phenyl)-3,4-dihydroisoquinolin-2-iums as novel antifungal lead compounds: Biological evaluation and structure-activity relationships

The title compounds are a class of structurally simple analogues of quaternary benzo[c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenylring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 mug/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2-12 exhibited excellentactivities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC50 values of 8.88-19.88 mug/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha- and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal agrochemicals. Compounds 8 and 2 should have great potential as new broad spectrum antifungal agents for plant protection.

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

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Use of aligned triphenylamine-based radicals in a porous framework for promoting photocatalysis

The Ca-MOF FIR-29 is synthesized and exhibits a honeycomb lattice of hexagonal channels with an aperture of ?16 A, giving a BET surface area of 2061 m2 g?1. The consecutive slipped pi¡¤¡¤¡¤pi stacking interactions of photoactive tris((4-carboxyl)phenylduryl)amine (TCPA) groups on the surface of hexagonal channels makes it an effective photocatalyst for catalyzing the typical Mannich photocatalysis, forming beta-tetrahydroisoquinolne ketones in high isolated yields. Catalytic activity for FIR-29 is about 2.7 times enhancement over that for mesoporous DUT-63 consisted of discrete TCPA groups without any intermolecular interaction. This is mainly due to the fact that the rigid compact stacking of tri([1,1?-biphenyl]-4-yl)amine (TBPA) is conducive to form stable TBPA radical, and is optimal for electron or energy transfer to expedite the reactivity of sp3 carbon atoms and allow higher photocatalytic conversion.

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

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Rhenium-catalyzed oxidative cyanation of tertiary amines with TMSCN

Oxidative cyanation of sp3 C-H bonds at the alpha position of tertiary amines by using TMSCN as the cyanide donor and a novel high-valent rhenium(V) complex was developed. The reaction offers the corresponding alpha-aminonitriles in good yields with tert-butyl hydroperoxide as the oxidant under mild and acid-free reaction conditions. Oxidative cyanation of sp3 C-H bonds at the alpha position of tertiary amines by using TMSCN as the cyanide donor and novel high-valent rhenium(V) complex catalysts is developed. The reactions offer the corresponding alpha-aminonitriles in good yields by using tert-butyl hydroperoxide as the oxidant under mild and acid-free reaction conditions at room temperature. Copyright

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

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Utilization of microflow reactors to carry out synthetically useful organic photochemical reactions

This review focuses on recent advances that have been made in conducting synthetically useful organic photochemical reactions by using microflow reactors. Attention is given to the utilization of this technique in the ?scale-up? of a variety of photochemical processes including intermolecular photocycloadditions, intramolecular photocycloadditions and photocyclizations, photoadditions, photoreductions, photoisomerizations, photosubstitutions, photooxidations, photorearrangements, and heterogeneous photocatalytic reactions. In many examples, the use of the microflow method is compared to those carried out in batch systems. Finally, advantages and disadvantages of microflow photoreactions along with the possible employment of this approach to scale-up industrial photochemical processes are discussed.

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A visible-light-promoted aerobic C-H/C-N cleavage cascade to isoxazolidine skeletons

The bicyclic isoxazolidine scaffolds are the ubiquitously recurring motifs in alkaloids. Despite of their facile biosynthesises in nature, the laboratory synthesis of these derivatives is still complicated. In this paper, the isoxazolidine derivatives are concisely constructed in one process with excellent stereoselectivity from simple tertiary amines through a C-H activation-retro-aza-Michael-oxidation-cyclization tandem sequence by means of visible-light. This protocol provides a concise approach to dactylicapnosinine derivatives.

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Double tooth Asia method for the preparation of phosphoric acid ester ligand buchwald – hartwig and the application of the catalyst in the reaction (by machine translation)

The invention discloses a novel double tooth Asia method for the preparation of phosphoric acid ester ligand Buchwald and the?Application of the catalyst in the reaction of Hartwig, which belongs to the field of organic synthetic chemistry. This invention is by the 3, 3 ‘, 5, 5′?Two Brothers butyl?2. 2’?Dihydroxy biphenyl and with different structure glycol is the two-step reaction of the raw material of the “one-pot synthesis” synthesized to obtain a series of novel double tooth Asia compound ligand phosphorus acid ester, the ligand of the kind is a kind of application a very wide range of compounds, it has the following structure. The advantage of this invention: biligand stable structure, simple and convenient synthesis, preparation of a large quantity of high yield. The ligand of this invention in the Pd catalyzed Buchwald?In the reaction of Hartwig has high reaction activity and substrate universality. (by machine translation)

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An efficient copper-catalyzed oxidative Mannich reaction between tertiary amines and methyl ketones

An efficient oxidative Mannich reaction between tertiary amines and unmodified methyl ketones has been developed, using copper salts as the catalyst and O2 as the oxidant. The Royal Society of Chemistry 2009.

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Tetrahydroisoquinoline – Wikipedia,
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Synthetic Transformations Using Molecular Oxygen-Doped Carbon Materials

Carbon materials like activated carbon (AC) undergo chemisorption with O2 to give species with electron deficiency in the carbon skeleton and negative charge at the oxygen end that upon reaction with PPh3 and benzoic acid afford Ph3P O. Whereas amine donors react with O2-chemisorbed AC and nucleophiles to give dehydrogenatively coupled products in 67-89% yields via the corresponding radical cation and iminium ion intermediates, the reactions using beta-naphthoxide derivatives give the corresponding oxidatively coupled bi-2-naphthol products in 68-95% yields.

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

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Controllable Chemoselectivity in Visible-Light Photoredox Catalysis: Four Diverse Aerobic Radical Cascade Reactions

Reported is the controllable selectivity syntheses of four distinct products from the same starting materials by visible-light photoredox catalysis. By employing a dicyanopyrazine-derived chromophore (DPZ) as photoredox catalyst, an aerobic radical mechanism has been developed, and allows the reactions of N-tetrahydroisoquinolines (THIQs) with N-itaconimides to through four different pathways, including addition-cyclization, addition-elimination, addition-coupling, and addition-protonation, with satisfactory chemoselectivity. The current strategy provide straightforward access to four different but valuable N-heterocyclic adducts in moderate to excellent yields. Radical control: A radical mechanism for N-tetrahydroisoquinolines (THIQ) in the presence of oxygen was successfully accomplished by employing a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst. The substrates can undergo either addition-cyclization, addition-elimination, addition-coupling, or addition-protonation by judiciously regulating the reaction conditions. Four types of N-heterocycles are generated in moderate to excellent yields.

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