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The 4-bora-3a,4a-diaza-s-indacene scaffold is known as Bodipy. 2,6-Diiodo-aza-Bodipy (B-1) and the Bodipy-2,6-diiodo-aza-Bodipy triad (B-2) have been used as novel photocatalysts for photoredox catalytic organic reactions with tetrahydroisoquiniline as substrate to prepare highly functionalized organic compounds via a [3 + 2] cycloaddition-aromatization tandem reaction and Cu(i)-catalyzed alkynylation reactions. In distinction to conventional photocatalysts such as Ru(bpy)3Cl2, Eosin Y or Rose Bengal, which are based on a mono-visible light-harvesting chromophore profile and show weak absorption in the visible region, the new photocatalysts are strong visible absorbers (B-1, epsilon = 73000 M-1 cm-1 at 683 nm). More importantly, resonance energy transfer (RET) has been used to increase the absorption of photocatalyst B-2 in the visible region, in which two Bodipy units were used as energy donor and diiodo-aza-Bodipy as energy acceptor. B-2 shows broadband absorption in the range 400-750 nm (epsilon = 165 000 M-1 cm-1 at 504 nm, and 71000 M-1 cm -1 at 683 nm). Iodo-aza-Bodipy is more efficient than conventional photocatalysts such as [Ru(bpy)3]Cl2. Furthermore, the broadband visible light-absorbing B-2 is more efficient as a photocatalyst than previously reported monochromophore photocatalyst B-4 (diiodo-Bodipy). Our results will be useful for the design of efficient organic triplet photosensitizers as photocatalysts for photoredox catalytic organic reactions. This journal is the Partner Organisations 2014.

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

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A dual catalytic system combining photoredox and Lewis base catalysis has been developed. By the appropriate choice of light source and catalyst, the photoredox cycle can be optimally modulated to match the base catalyzed reaction cycle to provide the corresponding products under mild reaction conditions.

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Eosin Y catalyzes efficiently the visible light mediated coupling of sp3 C-H bonds adjacent to the nitrogen atom in tetrahydroisoquinoline derivatives in the absence of an external oxidant. Nitroalkanes, dialkyl malonates, malononitrile, and dialkyl phophonates were used as pronucleophiles in this metal-free, visible light oxidative coupling reaction.

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

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The question of whether hydrogen atom transfer (HAT) or electron transfer (ET) is the key step in the activation of N-aryl tetrahydroisoquinolines in oxidative coupling reactions using CuBr as catalyst and tert-butyl hydroperoxide (tBuOOH) has been investigated. Strong indications for a HAT mechanism were derived by using different para-substituted N-aryl tetrahydroisoquinolines, showing that electronic effects play a minor role in the reaction. Hammett plots of the Cu-catalyzed reaction, a direct time-resolved kinetic study with in situ generated cumyloxyl radicals, as well as density functional calculations gave essentially the same results. We conclude from these results and from kinetic isotope effect experiments that HAT is mostly mediated by tert-butoxyl radicals and only to a lesser extent by tert-butylperoxyl radicals, in contrast to common assumptions. However, reaction conditions affect the competition between these two pathways, which can significantly change the magnitude of kinetic isotope effects.

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Tetrahydroisoquinoline – Wikipedia,
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The dehydrogenative a-phosphonation of substituted N,N-dialkylanilines by dialkyl H-phosphonates was achieved under mild conditions by using environmentally benign iron(II) chloride as catalyst and teri-butyl hydroperoxide as oxidant. The reaction proceeded in the presence of electron-donating (methoxy, methyl, benzyl) and electron-withdrawing ring-substitutents (bromo, carbonyl, carboxyl, m-nitro) in moderate to good yields. The X-ray crystal structure of N-(5,5-dimethyl-2-oxo- 2lambda5-[1,3,2]dioxaphosphinan-2-yl-methyl)-N-methyl-p-toluidine was determined. Bis-(4-(dimethylamino)phe- nyl)methane and bis-4,4′- (dimethylamino)benzophenone underwent bisphosphonation selectively by respective monophosphonation at the remote dimethylamino groups. Furthermore, the use of excess dialkyl H-phosphonate and oxidant allowed us to functionalize both methyl groups of N(CH3)2 in N,N-dimethyl-p-toluidine and N,N-dimethylaminomesidine, respectively, to obtain alpha,alpha?- bisphosphonatoamines in high yield.

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

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Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative alpha -cyanation of N-aryltetrahydroisoquinolines (THIQs) with trimethylsilyl cyanide (TMSCN), giving the corresponding products in good to excellent yields. Experimental investigations demonstrated that thiourea acts as a radical initiator by abstracting hydroxyl radical ([rad]OH) from tert-butyl hydroperoxide (TBHP) directly instead of non-covalent hydrogen bondings (H-bondings) activation. The use of thiourea as a radical initiator offers a new avenue for innovative chemical transformations in organocatalyzed radical chemistry.

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

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A useful method for molecular iodine catalyzed oxidative C-C bond formation between tertiary amines and a carbon nucleophile using hydrogen peroxide as the terminal oxidant is reported. This is the first report of a molecular iodine catalyzed cross-dehydrogenative coupling (CDC) reaction between two sp 3 C-H bonds.

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Tetrahydroisoquinoline – Wikipedia,
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We demonstrated that a cobalt(II)-TBHP (tert-butyl hydroperoxide) oxidizing system efficiently catalyzes the coupling of aromatic tertiary amines with enol silyl ethers, producing the corresponding beta-aminoketones.

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

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Porphyrin metal-organic frameworks (PMOFs) are emerging as heterogeneous photocatalysts owing to the well-designed frameworks incorporated with powerful light-harvesting porphyrin chromophores. The porous and stable framework Ir?PCN-224 (which is also denoted as Ir?PMOF-1), which has been prepared by the self-assembly of Ir(TCPP)Cl (TCPP=tetrakis(4-carboxyphenyl)porphyrin) and ZrCl4, is reported herein to be efficient for the aerobic cross-dehydrogenative carbon?phosphorus coupling reaction, giving rise to a high turn-over number (TON) of up to 17200 under visible light irradiation (lambda?420 nm). Electron paramagnetic resonance (EPR) experiments disclose that the active species might be the superoxide radical anion (O2 .?). Additionally, the intermediate imine cation has been detected by high-resolution mass spectrometry (HRMS).

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

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Chemical Research Letters, May 2021. Research speed reading in 2021. SDS of cas: 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

The combination of vanadium- and organocatalysis allows for the direct oxidative coupling of cyclic tertiary amines with non-activated ketones without the need for preformed leaving groups.

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