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Ligand- and Base-Free Copper(II)-Catalyzed C-N Bond Formation: Cross-Coupling Reactions of Organoboron Compounds with Aliphatic Amines and Anilines

(Equation presented) A ligandless and base-free Cu-catalyzed protocol for the cross-coupling of arylboronic acids and potassium aryltrifluoroborate salts with primary and secondary aliphatic amines and anilines is described. The process utilizes catalytic copper(II) acetate monohydrate and 4 A molecular sieves in dichloromethane at slightly elevated temperatures under an atmosphere of oxygen. A broad range of functional groups are tolerated on both of the cross-coupling partners.

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

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CBr4-mediated cross-dehydrogenative coupling reaction of amines

A novel CBr4-mediated dehydrogenative Povarov/aromatization tandem reaction of glycine derivatives with alkenes, leading to complex quinoline derivatives, and a CBr4-mediated dehydrogenative C?H functionalization of N-aryl tetrahydroisoquinolines with nucleophiles to form C?C and C?P bonds are reported. The reactions were performed under very simple and mild reaction conditions; only CBr4 was used as a promoter. A plausible mechanism involving a radical process is proposed.

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

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Construction of donor-acceptor type conjugated microporous polymers: A fascinating strategy for the development of efficient heterogeneous photocatalysts in organic synthesis

Metal-free, visible-light driven, solid organic photocatalysts provide a more green and environmentally friendly alternative to traditional metal-based photocatalysts. Donor-Acceepor (D-A) dyads possess a feature of easy to adjust the photoelectric properties, and enhance their photocatalytic performances. Here we report a fascinating strategy for screening excellent organic porous photocatalysts through oxidative coupling of single D-A based monomer, which has still an important advantage to ensure uniformity of polymer structure except for the inherent characteristics of D-A polymers. According to this strategy, three D-A typed conjugated microporous polymer (DA-CMP) photocatalysts consisting of alternating electron-rich (carbazole) and electron-deficient (benzene, 4,7-diphenyl-2,1,3-benzothiadiazole or anthraquinone) units have been synthesized, and their porosity and photoelectric properties including adsorption, emission, lifetime, optical bandgaps, energy levels and transient photocurrent response as well as photocatalytic activity, were conveniently tuned by selecting different D-A monomers with tunable electron-deficient moiety. These DA-CMPs were exploited as metal-free photocatalysts in the oxidative C-H functionalization reactions in the presence of visible-light and molecular oxygen. They showed excellent photocatalytic activity, extensive substrate adaptability and outstanding reusability, due to combining some key features like permanent porosity, outstanding stability and optoelectronic properties. In addition, the reaction mechanism for DA-CMP photocatalyzed C-H functionalization reactions under visible-light irradiation was investigated in detail. Moreover, to prove in depth the benefits of the heterogeneous photocatalysis, a continuous flow procedure has been conducted with an excellent yield.

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

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Making Copper(0) Nanoparticles in Glycerol: A Straightforward Synthesis for a Multipurpose Catalyst

Small zero-valent copper nanoparticles (CuNPs) have been straightforwardly prepared from Cu(I) and Cu(II) precursors in glycerol and in the presence of polyvinylpyrrolidone as stabilizer. Thanks to the negligible vapor pressure of the solvent, these original nano-systems could be directly characterized in glycerol as well as in the solid state, exhibiting relevantly homogeneous colloidal dispersions, also even after catalysis. CuNPs coming from the well-defined coordination complex di-mu-hydroxobis[(N,N,N?,N?-tetramethylethylenediamine)copper(II)] chloride {[Cu(kappa2-N,N-TMEDA)(mu-OH)]2Cl2} have been highly efficient in C?C and C?heteroatom bond formation processes. This new catalytic system has proved its performance in C?N couplings and in the synthesis of differently substituted propargylic amines through cross-dehydrogenative couplings, multi-component reactions such as A3 (aldehyde-alkyne-amine) and KA2 (ketone-alkyne-amine) couplings, as well as in the formation of heterocycles such as benzofurans, indolizines, and quinolines under smooth conditions. No significant copper amount was detected in the extracted organic compounds from the catalytic phase by inductively coupled plasma-atomic emission spectroscopic (ICP-AES) analyses, proving a highly efficient immobilization of copper nanoparticles in glycerol. From a mechanistic point of view, spectroscopic data (infrared and ultraviolet-visible spectra) agree with a surface-like catalytic reactivity. (Figure presented.).

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

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One-Pot Sequential Photoredox Chemistry and Asymmetric Transfer Hydrogenation with a Single Catalyst

A sequential process is reported, in which different photoredox reactions are placed in sequence with asymmetric transfer hydrogenations of aryl ketones to provide a diverse set of chiral alcohols with enantioselectivities of up to 99 % ee. The method relies on a single chiral-at-metal catalyst which is added at the beginning of the two step sequence and only a final purification of the reaction product is required.

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

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A mechanical to urge the enters the carbon – […] forming method (by machine translation)

The invention discloses a mechanical to urge the enters the carbon – […] forming method, said method comprising: in order to type 2 shown in formulae of organic amine 3 shown the chlorinated aromatic hydrocarbon as the raw material, the catalyst, ligand, in the presence of alkali and additive, the reaction is carried out by the mechanical grinding method, after the reaction mixture after the separation and purification, obtains the type 1 compound shown; in the present invention relates to mechanical grinding promotion to the chlorinated aromatic hydrocarbon as the substrate of the Buchwald – Hartwig reaction mainly adopts the organic phosphonate ligands, in the palladium catalyst under the action of the organic amine compound with the chlorinated aromatic hydrocarbon of the between the coupling, so as to obtain high yield of the target product, the majority of the reaction can be 90% or more yield. The mild reaction conditions, can be in the 1 – 2 H to complete the reaction. (by machine translation)

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

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Photocatalytic oxidative C-C bond formation

This chapter summarizes some important examples of carbon-carbon bond-forming reactions at the alpha-position of tertiary amines using photoredox catalysis. The photocatalytic single-electron oxidation of tertiary amines leads to the generation of an amine radical cation, from which two highly reactive and synthetically useful intermediates, iminium ions and alpha-aminoalkyl radicals, can be produced. Iminium ion intermediates, being electrophilic in nature, react with a range of carbon nucleophiles forming new carbon-carbon bonds. On the other hand, the alpha-aminoalkyl radical, an electron-rich radical, adds efficiently to electron-deficient unsaturated systems resulting in carbon-carbon bond-forming reactions. This chapter also highlights some examples of carbon-carbon bond-forming reaction by nucleophilic/radical addition to photocatalytically generated arene radical cations.

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

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Cu2O mesoporous spheres with a high internal diffusion capacity and improved catalytic ability for the aza-Henry reaction driven by visible light

Mesoporous Cu2O spheres with a large pore size (LP-Cu2O) bring out a better performance towards the photocatalytic aza-Henry reaction than Cu2O spheres with a small pore size (SP-Cu2O). This work highlights the internal diffusion coefficient as a critical parameter for the fabrication of porous photocatalysts. This journal is

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

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A TiO2 immobilized Ru(ii) polyazine complex: A visible-light active photoredox catalyst for oxidative cyanation of tertiary amines

A chemically functionalized nanocrystalline TiO2 grafted ruthenium(ii) polyazine complex was found to be an efficient visible light photoredox catalyst for the oxidative cyanation of tertiary amines to the corresponding alpha-aminonitriles in high to excellent yields, using molecular oxygen as an oxidant and sodium cyanide in acetic acid as a cyanide source. The developed photoredox catalyst could be easily recovered by simple filtration and reused for several runs with consistent catalytic activity.

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

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Visible light-mediated oxidative C(sp3)-H phosphonylation for alpha-aminophosphonates under oxidant-free conditions

An external oxidant-free synthesis of alpha-aminophosphonates by synergistically combining photocatalysis and proton-reduction catalysis is developed herein. The gram-scale experiment demonstrates the potential utility of this protocol. This study may have important implications for the functionalization of oxidant-sensitive C(sp3)-H bonds.

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