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Two cadmium(II) complexes with oxazoline-based ligands as effective catalysts for C-N cross-coupling reactions

Binuclear [{(DMOX)CdCl}2(mu-Cl)2] (DMOX = 4,5-dihydro-2-(4,5-dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyl-oxazole) (1) and mononuclear [(Dm-Pybox)CdCl2] (Dm-Pybox = 2,6-bis[4?,4?-dimethyloxazolin-2?-yl]pyridine) (2) were obtained by reacting CdCl2 with DMOX and Dm-Pybox ligands, respectively. In the solid state, the supramolecular structures of 1 and 2 feature helical chains fabricated by C-H-Cl hydrogen bond interactions. The C-N cross-coupling reactions catalyzed by the two complexes were also investigated in homogeneous system. The results show that binuclear complex 1 exhibit significantly enhanced catalytic activity for C-N cross-coupling reactions.

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

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Visible light mediated photocatalytic oxidative coupling reaction of N-phenyl tetrahydroisoquinoline with beta-keto acids

A visible light mediated photocatalytic oxidative coupling reaction of N-phenyl tetrahydroisoquinoline with beta-keto acids has been developed. This approach provides a mild and operationally simple access to the synthesis of C1-acylmethylated tetrahydroisoquinolines.

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

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Efficient C(sp 3)-H Bond Arylation of Tetrahydroisoquinolines with Knochel-Type Arylzinc Reagents under Oxidative Conditions

A novel C(sp 3)-H bond arylation of tetrahydroisoquinoline (THIQ) derivatives with Knochel-type arylzinc reagents has been developed. In the presence of MgCl 2, arylzinc reagents readily reacted with THIQ derivatives under oxidative conditions, affording a wide range of potentially biologically active compounds in good yields. Moreover, the developed method can tolerate a variety of sensitive functional groups such as an ester group.

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

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Angled Vortex Fluidic Mediated Multicomponent Photocatalytic and Transition Metal-Catalyzed Reactions

The dynamic thin film formed in an angled rapidly rotating tube in a vortex fluidic device (VFD) is effective in facilitating multicomponent reactions (MCRs) as photocatalytic or metal-mediated processes. Here, we demonstrate the utility of the VFD by using two known MCRs, an Ugi-type three component reaction and an A3-coupling reaction. The Ugi-type reaction can be done in either confined or continuous-flow modes of operation of the microfluidic platform whereas the A3-coupling reaction was optimized for the confined mode of operation. The examples tested gave excellent yields with short reaction times.

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

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N-substituted-3(10H)-acridones as visible-light photosensitizers for organic photoredox catalysis

N-Substituted-3(10H)-acridones have been established as visible-light organic photocatalyst. These photosensitizers are efficient for oxidative coupling reaction of N-aryl tetrahydroisoquinolines with various nucleophiles. Notably, N-methyl-3(10H)-acridone (Ia) is stable and can be effectively prepared. It is a water-soluble and atom-economic catalyst, and thus holds promise for green chemical applications. Mechanistic studies confirm a single electron transfer (SET)-induced radical process and a rate-limiting step. Analysis of the photocatalytic reactivity?structure relationship reveals that the acridones are robust and tunable photosensitizers for photoredox catalysis.

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

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Highly efficient and recyclable magnetic nanoparticles-supported gold(III)-bipy catalyst for oxidative alpha-cyanation of tertiary amines

Oxidative alpha-cyanation of tertiary amines with trimethylsilyl cyanide was achieved by using a magnetic nanoparticles-supported gold(III)-bipy complex as catalyst to afford the corresponding alpha-aminonitriles in good to excellent yields in the presence of tert-butyl hydroperoxide under acid-free conditions. The new heterogeneous gold catalyst can easily be separated from the reaction mixture by using an external magnet and can be recycled for at least 10 times without any loss of activity.

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

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Catalytic asymmetric ¡À-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis

Cross-coupling reactions are among the most widely utilized methods for C-C bond formation; however, the requirement of preactivated starting materials still presents a major limitation. Methods that take direct advantage of the inherent reactivity of the C-H bond offer an efficient alternative to these methods, negating the requirement for substrate preactivation. In this process, two chemically distinct activation events culminate in the formation of the desired C-C bond with loss of H2 as the only byproduct. Herein we report the catalytic asymmetric ¡À-acylation of tertiary amines with aldehydes facilitated by the combination of chiral N-heterocyclic carbene catalysis and photoredox catalysis.

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

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A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions

A versatile aerobic catalytic system (I2 and O2/TBHP) for C-H functionalization is reported. This CDC (cross-dehydrogentive coupling) reaction is compatible with a large number of nucleophiles and is performed under ambient reaction conditions. The scope of the metal-free CDC is illustrated by synthesizing a variety of functionalized tetrahydroisoquinolines and N,N-dimethylaniline. The highlight of the method is a Friedel-Crafts reaction of phenols and indole with tertiary amines.

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