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Mechanochemical Oxidative Mannich Reaction: Evaluation of Chemical and Mechanical Parameters for the Mild and Chemoselective Coupling of N-tert-butoxycarbonyltetrahydroquinolines and Ketones

A mechanochemical oxidative Mannich reaction of N-tert-butoxycarbonyl (Boc) tetrahydroquinolines and ketones was successfully developed under solvent-free ball-milling conditions. The reaction afforded the desired coupling products in satisfactory yields under mild and tractable oxidative conditions. Side reactions such as deprotection of the Boc group were prevented by carefully adjusting the milling parameters, including milling frequency, time, milling-ball filling degree, milling-ball size, and grinding auxiliary. Further examination of the scope indicated that the reaction system could also be applied to the N-benzyloxycarbonyl and N-aryl substrates to afford the corresponding products in moderate to good yields.

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

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Pd-catalyzed synthesis of aryl amines via oxidative aromatization of cyclic ketones and amines with molecular oxygen

Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of amines with nonaromatic ketones. Under optimized reaction conditions, primary and secondary amines are selectively arylated in good yields with cyclohexanones and 2-cyclohexen-1-ones in the presence of a Pd-catalyst under an atmosphere of molecular oxygen.

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

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Based on benzothiazole unit a covalent organic framework material synthetic method (by machine translation)

The invention discloses a covalently bound based on benzothiazole unit method for synthesizing organic framework material, comprising the following steps: in an organic solvent or in ionic liquid, 2, 4, 6-trihydroxy are three phenyltheophylline formaldehyde and 2,6-diaminobenzene and b thiazole reaction to obtain the organic framework material of covalency. The method to obtain covalent organic framework material has relatively large specific surface area and pore structure of the rules, it is a kind of good photocatalyst material, can be used for the photocatalytic N-aryl tetrahydroisoquinoline cross-dehydrogenation coupling reaction, has good stability and excellent catalytic effect. (by machine translation)

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

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Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4- benzoquinone oxidation under mild conditions

The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction between readily available aryl Grignard reagents and iminium (or oxonium) cations generated in situ by DDQ oxidation of tetrahydroisoquinolines (or isochromans) under mild conditions.

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

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Enantioselective synthesis of 2-substitued-tetrahydroisoquinolin-1-yl glycine derivatives via oxidative cross-dehydrogenative coupling of tertiary amines and chiral nickel(II) glycinate

The asymmetric synthesis of 2-substituted-tetrahydroisoquinolin-1-yl glycines was achieved by an oxidative cross-dehydrogenative coupling (CDC) reaction. This method for activation of the alpha-C-H bonds of amines with chiral nickel(II) glycinate using o-chloranil as the sole oxidant afforded highly diastereoselective coupling adducts. The decomposition of coupling adducts readily afforded 2-substituted-tetrahydroisoquinolin-1-yl glycine derivatives.

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

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For visible light catalytic metal organic framework material and its synthetic method and application (by machine translation)

This invention relates to a kind of used for visible light catalytic metal organic framework material and its synthetic method and application. The method comprises the following steps: the two organic ligand H 2 1 and H 2 2 in N, N-dimethyl formamide (DMF) solvent after uniformly mixing, adding ZrCl 4, in acetic acid under the control of the metal-organic framework material is obtained by reacting UIO-68Se, wherein the molar ratio of the two kinds of organic ligand 1:1-1:4. The material can be used as a visible-light responsive photocatalyst, the catalytic under the environment of air occurs and a nucleophilic reagent addition a cross-coupling reaction. The invention is based on the metal organic framework material having photocatalyst activity is high, the circulating is good, strong stability, easy separation and recycling, and the like. (by machine translation)

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

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Tuning PtII-Based Donor?Acceptor Systems through Ligand Design: Effects on Frontier Orbitals, Redox Potentials, UV/Vis/NIR Absorptions, Electrochromism, and Photocatalysis

Asymmetric platinum donor?acceptor complexes [(pimp)Pt(Q2?)] are presented in this work, in which pimp=[(2,4,6-trimethylphenylimino)methyl]pyridine and Q2?=catecholate-type donor ligands. The properties of the complexes are evaluated as a function of the donor ligands, and correlations are drawn among electrochemical, optical, and theoretical data. Special focus has been put on the spectroelectrochemical investigation of the complexes featuring sulfonyl-substituted phenylendiamide ligands, which show redox-induced linkage isomerism upon oxidation. Time-dependent density functional theory (TD-DFT) as well as electron flux density analysis have been employed to rationalize the optical spectra of the complexes and their reactivity. Compound 1 ([(pimp)Pt(Q2?)] with Q2?=3,5-di-tert-butylcatecholate) was shown to be an efficient photosensitizer for molecular oxygen and was subsequently employed in photochemical cross-dehydrogenative coupling (CDC) reactions. The results thus display new avenues for donor?acceptor systems, including their role as photocatalysts for organic transformations, and the possibility to introduce redox-induced linkage isomerism in these compounds through the use of sulfonamide substituents on the donor ligands.

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

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Highly efficient copper-catalyzed nitro-Mannich type reaction: Cross-dehydrogenative-coupling between sp3 C-H bond and sp 3 C-H bond

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

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Metal-organic framework composites with luminescent gold(iii) complexes. Strongly emissive and long-lived excited states in open air and photo-catalysis

The encapsulation of luminescent gold(iii) complexes by metal-organic frameworks (MOFs) lays the groundwork for new phosphorescent materials with activities that are not readily achieved by the host MOF materials or gold(iii) complexes alone. In this work, strong phosphorescence with lifetimes of up to ?50 mus in open air at room temperature has been achieved by incorporation of cationic cyclometalated gold(iii) complexes into MOFs with anionic frameworks to form AuIII@MOFs. The AuIII@MOFs display solid state two-photon-induced phosphorescence. Photo-reduction of methyl viologen to the reduced radical was achieved inside AuIII@MOFs and in the presence of Et3N upon excitation at lambda > 370 nm under ambient conditions. These AuIII@MOFs comprise a class of reusable and size-selective heterogeneous photo-catalysts for the aerobic oxidation of secondary amines to imines as well as five other reactions, including oxidative C-H functionalization under aerobic conditions.

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

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Antimony/N-hydroxyphthalimide as a catalyst system for cross- dehydrogenative coupling reactions under aerobic conditions

In the course of our investigations to find a novel catalyst for the cross-dehydrogenative coupling (CDC) reaction, it was discovered that antimony(V) serves as a co-catalyst with N-hydroxyphthalimide (NHPI) under aerobic conditions. This is a rare example of a catalytic use of antimony for an oxidative coupling reaction.

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