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A convenient and efficient method for oxidative coupling of tetrahydroisoquinoline derivatives with trimethyl(trifluoromethyl)silane and terminal alkynes to 1-trifluoromethylated or 1-alkynylated tetrahydroisoquinolines via CH activation was developed using visible light irradiation. The protocol uses Rose Bengal as the catalyst, air as terminal oxidant, and the trifluoromethylation or alkynylation was selectively performed at the alpha-position of nitrogen under extremely mild conditions.

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

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A wide range of catalysts based on supported copper nanoparticles have been prepared and tested in the cross-dehydrogenative coupling of tertiary amines and terminal alkynes. Copper nanoparticles on zeolite Y were found to be the most effective catalyst in the presence of tert-butyl hydroperoxide as the oxidant. Contrary to the previously reported methodologies involving copper catalysts, reactions have been accomplished without the need of an inert atmosphere and in the absence of solvent, using 1.5mol% catalyst. A variety of tertiary amines, including aromatic, benzylic and aliphatic ones, have been coupled with both aromatic and aliphatic alkynes to furnish the corresponding propargylamines in moderate-to-excellent yields. The procedure has been successfully scaled-up to 12mmol with a high conversion (93%). Moreover, the catalyst has been reused in seven cycles maintaining a good performance. Its catalytic activity has been compared with that of an array of commercial copper catalysts, being superior as regards the conversion and minimizing the alkyne homocoupling as a side reaction. The negative filtration test points to a heterogeneous nature of the process. Based on compelling experimental evidence, a novel reaction mechanism has been delineated which outlines the essential role of free radicals and the couple copper(I)/copper(II).

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

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A direct vinylogous cross-dehydrogenative coupling (CDC) reaction of N-aryl tetrahydroisoquinolines with 3,5-dialkyl-4-nitroisoxazoles catalysed by CuBr using air as the oxidant in water has been developed. This new strategy provides an efficient and environmentally benign way to access medicinally important isoxazole substituted tetrahydroisoquinoline derivatives under mild conditions.

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Tetrahydroisoquinoline – Wikipedia,
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An intermolecular radical-radical cross-coupling reaction of secondary and tertiary amines with aryl ketones and aldehydes has been developed using visible light photoredox catalysis. This reaction provides an efficient and straightforward approach to some useful 1,2-amino alcohols in moderate to good yields under mild conditions.

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Copper catalysed phenylation of aromatic and aliphatic amines using phenyllead triacetate has been compared with the analogous reactions using five-valent bismuth derivatives.

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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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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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Development of cross-coupling chemistry by direct functionalization of C-H or heteroatom-H bonds under oxidative conditions proved to be ideal method for the construction of C-C and C-heteroatom bonds in recent times. Several transition metal catalysts were successfully utilized for these kind of transformations over the past several years. Among them, copper salts are of special importance because of their easy availability, biocompatibility and economical advantages. This review summarizes the current trends in Cu-catalyzed inter and intramolecular reactions under oxidative dehydrogenation process in achieving C-C, C-O, C-N, C-S and C-P bond formations over the past 3 years.

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

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Our previous studies into visible-light-mediated aza-Henry reactions demonstrated that molecular oxygen played a vital role in catalyst turnover as well as the production of base to facilitate the nucleophilic addition of nitroalkanes. Herein, improved conditions for the generation of iminium ions from tetrahydroisoquinolines that allow for versatile nucleophilic trapping are reported. The new conditions provide access to a diverse range of functionality under mild, anaerobic reaction conditions as well as mechanistic insights into the photoredox cycle.

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

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A simple and efficient cobalt-catalyzed aerobic oxidative dehydrogenative Povarov reaction of tertiary anilines with dihydrofuran has been developed for the synthesis of hexahydrofuro[3,2-c]quinolines. The one-electron-oxidation involved reaction is performed under mild conditions and only requires simple cobalt salts as a catalyst and dioxygen as a terminal oxidant.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
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