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Iodo-Bodipys were used as organic catalysts for three different photoredox catalytic organic reactions, i.e. the aza-Henry reaction of tetrahydroisoquinoline, oxidation/[3 + 2] cycloaddition/oxidative aromatization tandem reaction between tetrahydroisoquinolines and maleimides, and C-H arylation of heteroarenes with diazonium salts. The organic photocatalysts act as either electron acceptors (reductive quenching) or electron donors (oxidative quenching) in the single electron transfer (SET) of the catalytic cycles. Different from the widely used Ru(bpy)3[PF6]2, Ir(ppy)3, or halo-xanthane photocatalysts (Eosin Y or Rose Bengal), the new organic photocatalysts show strong absorption of visible light and long-lived triplet excited states, which are beneficial for SET, a crucial step for photoredox catalytic organic reactions. Moreover, the molecular structures of the new photocatalysts can be easily modified, as a result the absorption wavelength of the photocatalysts was readily tuned from 529 nm to 630 nm. The three different types of organic reactions are accelerated with the new organic photocatalysts (typical reaction times 1-2 h) compared to that catalyzed by Ru(bpy)3[PF6]2 or Ir(ppy)3 (reaction time: 12-72 h). The C-H arylation of thiophene with phenyl diazonium salts was used to prepare new Bodipy derivatives that show large Stokes shift. Our results are useful for designing of new organic catalysts for photoredox catalytic organic reactions to prepare highly functionalize organic compounds.

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

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In contrast to previous studies, we disclose for the first time that the singlet excited state (1PS?) of BODIPY rather than the triplet excited state (3PS?) can drive C-H bond activation to form C-C and C-P bonds smoothly, which offers new methods to promote organic transformation under visible light irradiation.

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

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

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A gold-catalyzed cyclization of 1-alkynyl-2-aryl tetrahydroisoquinolines is described for the synthesis of novel dihydrodibenzoquinolizinium salts. The reaction mechanism is likely to involve a 6-endo-dig cyclization and subsequent oxidation by air to give a relatively stable arylgold intermediate. This gold species undergoes protodeauration under acidic conditions to afford the title compounds. An NMR study was performed to gain further evidence and insight on the presence of the arylgold intermediate and the reaction mechanism. (Figure presented.).

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

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The efficient thiourea-catalyzed cross-dehydrogenative coupling of C(sp3)?H with diethyl phosphite by using tert-butyl peroxide as a terminal oxidant was explored. This protocol further expands the application scope of H-bond donors and also provides facile access to biologically relevant alpha-amino phosphonic derivatives.

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

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In this communication we describe the oxidative C-C bond formation of tertiary amines with various nucleophiles under very mild and environmental friendly conditions by using mesoporous graphitic carbon nitride (mpg-C 3N4) semiconductor as a heterogeneous, metal-free photosensitizer in combination with visible light and oxygen as the terminal oxidation agent. This system can be further combined with proline- organocatalysis to achieve oxidative tandem photocatalysis, demonstrating a rich cascade of chemical possibilities of the current photosynthesis system. Copyright

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

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Enantioselective C-C bond formations between the sp3 C-H bond of prochiral CH2 and terminal alkynes via the cross-dehydrogenative coupling (CDC) reaction were studied. Efficient asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives were achieved by using a catalytic amount of CuOTf together with PyBox chiral ligand. When dihydroisoquinolinium salts were used as electrophiles, the combination of CuBr/QUINAP provided the best results for asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives. The factors influencing the enantioselectivity were studied.

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Tetrahydroisoquinoline – Wikipedia,
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A novel C-C bond formation method was developed via the cross-dehydrogenative-coupling (CDC) reaction catalyzed by using copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct beta-nitroamine via the reaction between sp3 C-H and sp3 C-H bonds. Copyright

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

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A series of cyclometalated PdII complexes that contain pi-extended R-C^N^N-R? (R-C^N^N-R?=3-(6?-aryl-2?- pyridinyl)isoquinoline) and chloride/pentafluorophenylacetylide ligands have been synthesized and their photophysical and photochemical properties examined. The complexes with the chloride ligand are emissive only in the solid state and in glassy solutions at 77 K, whereas the ones with the pentafluorophenylacetylide ligand show phosphorescence in the solid state (lambdamax=584-632 nm) and in solution (lambdamax=533- 602 nm) at room temperature. Some of the complexes with the pentafluorophenylacetylide ligand show emission with lambdamax at 585-602 nm upon an increase in the complex concentration in solutions. These PdII complexes can act as photosensitizers for the light-induced aerobic oxidation of amines. In the presence of 0.1 mol % PdII complex, secondary amines can be oxidized to the corresponding imines with substrate conversions and product yields up to 100 and 99 %, respectively. In the presence of 0.15 mol % PdII complex, the oxidative cyanation of tertiary amines could be performed with product yields up to 91 %. The Pd II complexes have also been used to sensitize photochemical hydrogen production with a three-component system that comprises the PdII complex, [Co(dmgH)2(py)Cl] (dmgH=dimethylglyoxime; py=pyridine), and triethanolamine, and a maximum turnover of hydrogen production of 175 in 4 h was achieved. The excited-state electron-transfer properties of the PdII complexes have been examined. Copyright

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

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?Sunflow? ? The combination of a microcapillary reactor in continuous flow mode with sunlight as the most sustainable energy source imaginable was applied to a range of photoredox and H-atom-transfer reactions making them both fast and green.

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