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Nickel(II) tetraphenylporphyrin (NiTPP) is presented as a robust, cost-effective and efficient visible light induced photoredox catalyst. The ground state electrochemical data (CV) and electronic absorption (UV-Vis) spectra reveal the excited state redox potentials for [NiTPP]*/[NiTPP].? and NiTPP].+/[NiTPP]* couples as +1.17 V and ?1.57 V vs SCE respectively. The potential values represent NiTPP as a more potent photocatalyst compare to the well-explored [Ru(bpy)3]2+. The non-precious photocatalyst exhibits excited state redox reactions in dual fashions, i. e., it is capable of undergoing both oxidative as well as reductive quenching pathways. Such versatility of a photocatalyst based on first-row transition metals is very scarce. This unique phenomenon allows one to perform diverse types of redox reactions by employing a single catalyst. Two different sets of chemical reactions have been performed to represent the synthetic utility. The catalyst showed superior efficiency in both carbon-carbon and carbon-heteroatom bond-forming reactions. Thus, we believe that NiTPP is a valuable addition to the photocatalyst library and this study will lead to more practical synthetic applications of earth-abundant-metal-based photoredox catalysts. (Figure presented.).

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

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A new efficient DEAD-promoted oxidative Ugi/Wittig reaction for the preparation of 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles has been developed. The one-pot reactions of odorless isocyano(triphenylphosphoranylidene)acetates, carboxylic acids, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced polysubstituted 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles directly in good yields in the presence of DEAD oxidant.

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Construction of porous organic polymers (POPs) as metal-free heterogeneous organic photocatalysts for highly efficient catalytic organic transformations using visible light remains a key challenge. Herein, we report the ?bottom-up? strategy to facilely synthesize two Eosin Y dye-based POP frameworks (EY-POPs) for highly efficient heterogeneous organic-photocatalysis. Owing to the high BET surface area and the built-in character of the covalently linked catalytic sites of EY-POPs, these photoactive polymers show excellent catalytic activity in photocatalyzing the aza-Henry reaction. The superior utility of the EY-POP-1 polymer in catalysis was demonstrated by the broad scope of the reactants and the high yield of the reaction products. Moreover, the EY-POP-1 polymer shows robust recycling capability with good retention of photoactivity over at least twelve cycles without any significant loss of the catalytic activity (94-98% yield).

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

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This work shows that a deprotection strategy of BODIPY conjugated porous polymers (CMPBDPs) can be successfully applied to synthesize a new (dipyrrin)(bipyridine)Ru(ii) (CMPBDP-Ru) efficient heterogeneous photocatalyst for iminium ion generation under visible light. CMPBDP-Ru shows high thermal and photochemical stability under irradiation, and it could be reused several times.

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Tetrahydroisoquinoline – Wikipedia,
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We report an efficient enantioselective conjugate addition of photogenerated alpha-amino radicals to Michael acceptors catalyzed by a newly prepared chiral-at-metal rhodium complex. This protocol shows that a single Rh(iii) complex can serve not only as a Lewis acid but also as a photoredox catalyst to control the stereoselectivity during the bond formation.

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

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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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This review gives a comprehensive treatment to show and illustrate current efforts in the field of recyclable catalysis. Results of recycling studies performed with a wide range of soluble homogeneous and immobilized complexes as well as heterogeneous catalysts developed in recent years have been collected and discussed. Among others, transformations including hydrogenation, reduction, oxidation, varied asymmetric syntheses and coupling reactions are covered. A thorough analysis of the available data and discussion of issues related to recyclability in general are also given. The review includes selected literature examples until the beginning of 2017.

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The N-arylation of aliphatic and aromatic amines by Ph3Bi and Cu(OCOR)2 gives high yield of the mono- or di-phenylated amines under mild conditions.

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

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Metal-free consecutive C(sp2)-X (X = Cl, Br, S, N) bond formations of N-aryl amines (cyclic, fused, carbamate, and aminium radicals) were achieved under mild conditions using [bis(trifluoroacetoxy)iodo]benzene (PIFA) and simple nonharmful sodium salts. This direct and selective C(sp2)-H functionalization showed excellent functional group compatibility, cost effectiveness, and late-stage applicability for the synthesis of biologically active natural products. Two mechanisms were proposed to explain the ortho- or para-preference, as well as the accelerating effect of CH3NO2

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

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The ionic liquid 1-butyl-3methylimidazolium tetrafluoroborate [BMIm][BF4] has demonstrated high efficiency when applied as a solvent in the oxidative nitro-Mannich carboncarbon bond formation. The coppercatalyzed cross-dehydrogenative coupling (CDC) between N-phenyltetrahydroisoquinoline and nitromethane in [BMIm][BF4] occurred with high yield under the described reaction conditions. Both the ionic liquid and copper catalyst were recycled nine times with almost no lost of activity. The electrochemical behavior of the tertiary amine substrate and beta-nitroamine product was investigated employing [BMIm][BF4] as electrolyte solvent. The potentiostatic electrolysis in ionic liquid afforded the desired product with a high yield. This result and the cyclic voltammetric investigation provide a better understanding of the reaction mechanism, which involves radical and iminium cation intermediates.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
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