Access to [2.2]Paracyclophane-Fused N-Heterocycles via Palladium-Catalyzed C–H Activation and Cyclization of [2.2]Paracyclophaneacylhydrazones with Vinyl Azides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 13, 2025

A novel protocol for the synthesis of [2.2]paracyclophane-fused N-heterocycles via palladium-catalyzed C-H activation and cyclization [2.2]paracyclophaneacylhydrazones with vinyl azides has been developed. High regioselectivity control was realized by selective activation/functionalization bond highly rigid [2.2]paracyclophanes. broad range isoquinolinophane derivatives were prepared in sole good functional group tolerance, which would be difficult to synthesize other approaches a one-step manner.

Language: Английский

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Asymmetric Transfer Hydrogenation of 2-Substituted Quinoxalines with Regenerable Dihydrophenanthridine

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3666 - 3671

Published: Feb. 15, 2024

The asymmetric hydrogenation of quinoxalines represents one the most efficient approaches for synthesis optically active tetrahyroquinoxalines. In this paper, we demonstrate a metal-free transfer 2-substituted with regenerable dihydrophenanthridine under H2 using combination chiral phosphoric acid and achiral borane as catalysts. A wide range tetrahydroquinoxalines were produced in high yields ≤98% ee.

Language: Английский

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Reserving Electrons in Cofactor Decorated Coordination Capsules for Biomimetic Electrosynthesis of α-Hydroxy/amino Esters

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

Sustainable electricity-to-chemical conversion via the utilization of artificial catalysts inspired by redox biological systems holds great significance for catalyzing synthesis. Herein, we develop a biomimetic electrosynthesis strategy mediated nicotinamide adenine dinucleotide (NADH) mimic-containing coordination capsule efficiently producing α-hydroxy/amino esters. The saturated metal centers worked as an electron relay to consecutively accept single electrons while donating two NAD

Language: Английский

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Synthesis of [2.2]Paracyclophane-Fused Heterocycles via Palladium-Catalyzed C–H Activation/Annulation of [2.2]Paracyclophanecarboxamides with Arynes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2387 - 2392

Published: March 15, 2024

[2.2]Paracyclophane-fused heterocycles represent an important scaffold. Traditional approaches often suffer from tedious synthetic routes, and the development of catalytic synthesis them remains in its infancy. Herein, by employing highly strained aryne intermediates as partners, we have developed a concise protocol palladium-catalyzed C–H activation/annulation [2.2]paracyclophanecarboxamide substrates. quinolinone products are obtained good yields (up to 84%). Furthermore, utility process has been shown through [2.2]paracyclophane-fused heterocyclic catalysts.

Language: Английский

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Biomimetic Frustrated Lewis Pair Catalysts for Hydrogenation of CO to Methanol at Low Temperatures

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 4(2), P. 258 - 267

Published: Jan. 31, 2024

The industrial production of methanol through CO hydrogenation using the Cu/ZnO/Al2O3 catalyst requires harsh conditions, and development new catalysts with low operating temperatures is highly desirable. In this study, organic biomimetic FLP good tolerance to poison are theoretically designed. base-free catalytic reaction contains 1,1-addition into a formic acid intermediate methanol. Low-energy spans (25.6, 22.1, 20.6 kcal/mol) achieved, indicating that can be hydrogenated at temperatures. extended aromatization–dearomatization effect involving multiple rings proposed effectively facilitate rate-determining step, activation model for catalysts.

Language: Английский

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Progress in Asymmetric Hydrogenation of Aromatic N-Heterocyclic Compounds

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1403 - 1403

Published: Jan. 1, 2024

The structure of chiral saturated N-heterocyclic compounds widely exists in natural products, bioactive molecules, and drug molecules.Catalytic asymmetric hydrogenation aromatic N-heterocycles is one the most effective methods for construction these compounds.However, due to strong conjugation stability nitrogen-containing heterocyclic poison effect nitrogen atoms products on metal catalysts, development reactions lags far behind, there are relatively few research reports.Therefore, how develop efficient catalytic systems activate inert substrate precisely control stereoselectivity reaction key scientific issue relevant research.In recent years, a series organo catalysts has led significant progress shown broad prospects its applications.Considering that structures properties different have remarkable influence reactivity, selectivity, generality target transformations, an overview categorized provided according types catalysts.

Language: Английский

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Manganese Pentacarbonyl Bromide as Regeneration Catalyst Enabled Biomimetic Asymmetric Reduction

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2535 - 2539

Published: March 25, 2024

Using readily available manganese pentacarbonyl bromide as a regeneration catalyst, biomimetic asymmetric reduction of imines including quinoxalinones, benzoxazinones, and benzoxazine has been successfully developed in the presence transfer catalyst chiral phosphoric acids, providing amines with high yields enantioselectivities.

Language: Английский

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Reduction of C=N to CHNH by Metal-Catalyzed Hydrogenation and Transfer Hydrogenation

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

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