Recent Advances in C–H Activation for the Synthesis of π-Extended Materials

ACS Materials Letters, Journal Year: 2020, Volume and Issue: 2(8), P. 951 - 974

Published: June 29, 2020

The activation of typically unreactive aromatic C–H bonds by transition-metal catalysis has been receiving increased attention from the synthetic chemistry community in recent years. Advances this area have enabled direct and site-selective modification rings without need for pre-functionalization. Accordingly, these techniques found broad application many fields, including construction extended π-systems use materials science. This review will discuss reports reactions applied toward synthesis π-extended functional materials.

Language: Английский

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Palladium-catalyzed cross-dehydrogenative coupling of (hetero)arenes

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1495 - 1622

Published: Jan. 1, 2024

A general and authoritative literature overview on Pd-catalyzed cross-dehydrogenative coupling reactions of (hetero)arenes from the origins to 2023, where not only synthetic aspects were described but also most relevant mechanistic features.

Language: Английский

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Advances in C(sp²)−H/C(sp²)−H Oxidative Coupling of (Hetero)arenes Using 3d Transition Metal Catalysts

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(8), P. 1998 - 2022

Published: March 3, 2021

Abstract C−H/C−H oxidative coupling has emerged as a straightforward and powerful technique for the construction of (hetero)biaryls, with substantial application to drug discovery, agrochemicals, biology, material sciences. Mainly aryl‐aryl, aryl‐heteroaryl, heteroaryl‐heteroaryl couplings via double C( sp 2 )−H activation using 4d or 5d noble transition metal catalysts have been extensively studied. Considering earth‐abundant inexpensive nature 3d metals, sustainable development )−H/C( employing such gained significant attention. In this review, we present comprehensive overview (hetero)arenes catalyzed by metals. magnified image

Language: Английский

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Transition metal pincer complexes: A series of potential catalysts in C H activation reactions

Coordination Chemistry Reviews, Journal Year: 2022, Volume and Issue: 475, P. 214915 - 214915

Published: Oct. 31, 2022

Language: Английский

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Synthesis of Unsymmetrical Biheteroarenes via Dehydrogenative and Decarboxylative Coupling: a Decade Update

The Chemical Record, Journal Year: 2021, Volume and Issue: 22(4)

Published: Dec. 30, 2021

Abstract The design and development of robust efficient methods for installing one heterocycle with another is endowed as a ubiquitous powerful synthetic strategy to access complex organic biheterocycles in recent days due their pervasive applications medicinal well material chemistry. This perspective presents an overview on the findings developments synthesis unsymmetrical biheteroarenes via dehydrogenative decarboxylative couplings literature coverage mainly extending from 2011 2021. For simplification readers, article has been subcategorized based catalysts used reactions.

Language: Английский

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Homogeneous and Recyclable Palladium Catalysts: Application in Suzuki–Miyaura Cross-Coupling Reactions

Organometallics, Journal Year: 2023, Volume and Issue: 42(17), P. 2353 - 2358

Published: Aug. 23, 2023

This work demonstrates the use of catalytic systems that take advantage a metalla-GAP strategy (GAP = group-assisted purification) in homogeneous catalysis. discovery allows simple reclamation and reuse metal catalysts. Homogeneous catalysis has many appealing properties, such as high chemo-, regio-, stereoselectivity, an abundance suitable catalysts to choose from, generally mild reaction conditions. However, catalyst cannot be used more practical, industrially relevant settings because poor separability between products catalyst. The m-GAP is demonstrated palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. Excellent recyclability synthetic utility are observed these transformations.

Language: Английский

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Palladium(II) NCS‐Pincer Complexes Mediated Regioselective Cross Dehydrogenative Alkenation of 2‐Arylthiophenes

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: March 18, 2024

Abstract In this report, we have synthesized two new NCS pincer ligands by the Schiff base reaction of 3‐((phenylthio)methoxy)benzaldehyde ( P ) with alkyl amines t butylamine L1 and 1‐adamantylamine L2 )). The palladium complexes butylamine= C1 1‐adamantylamine= C2 these were their PdCl 2 (CH 3 CN) precursor. newly characterized using various analytical spectroscopic techniques such as 1 H, 13 C{ H} Nuclear Magnetic Resonance (NMR), Ultraviolet–visible (UV‐Visible), Fourier Transform Infrared (FTIR) Spectroscopy, High‐Resolution Mass Spectrometry (HRMS). structure ligand its coordination mode precursor studied help single‐crystal X‐ray diffraction. showed distorted square planar geometry around center. used catalysts for regioselective cross‐dehydrogenative alkenation 2‐arylthiophene derivatives. complex , where sterically bulky adamantyl is part side arm a higher yield reaction. Only 2.5 mol% catalyst loading was sufficient to achieve 74–95 % yields desired products excellent functional group tolerance under mild conditions. poisoning experiments (PPh Hg) homogeneous nature catalytic process. plausible mechanism proposed based on control time‐dependent HRMS studies.

Language: Английский

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Synthesis, Characterization and Application of NNN Pincer Manganese Complexes with Pyrazole Framework in α-Alkylation Reaction

Molecules, Journal Year: 2025, Volume and Issue: 30(7), P. 1465 - 1465

Published: March 26, 2025

A series of novel NNN pincer manganese complexes based on pyrazole skeleton 4 were efficiently synthesized in a two-step process. All the new fully characterized by 1H, 13C NMR spectra. Furthermore, molecular structures 4a and 4c also determined X-ray single-crystal diffraction. The manganese(I) catalysts obtained showed efficient catalytic activity α-alkylation reaction ketones with alcohols. Under optimal conditions, expected products procured moderate to high yields.

Language: Английский

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Unsymmetrical NNE (E = S, Se) Pincer Palladium(II) Complexes: Syntheses, Structure, and Catalytic Activity in Decarboxylative Heteroarylation of Coumarin-3-carboxylic Acids

Organometallics, Journal Year: 2025, Volume and Issue: unknown

Published: April 4, 2025

Language: Английский

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Palladium complexes containing NNN pincer type ligands and their activities in Suzuki-Miyaura cross coupling reaction

Heliyon, Journal Year: 2023, Volume and Issue: 9(7), P. e17608 - e17608

Published: June 27, 2023

Five new NNN pincer-type ligands and their palladium complexes were successfully synthesised characterised by FT-IR, 1H NMR, 13C UV–vis analyses. TEM analysis was used to observe the morphological character of black residues obtained from fourth cycle reusability test. Furthermore, suitable crystals N2,N6-bis(2-tert-butylphenyl)pyridine-2,6-dicarboxamide its complex elucidated with X-ray single crystal diffraction method. Both ligand crystallise in a monoclinic system space group P21/c for H2L4 C2/c complex. The structure pincer stabilised intramolecular intermolecular C–H⋅⋅⋅O, C–H⋅⋅⋅N, N–H⋅⋅⋅N contacts. A Suzuki-Miyaura cross-coupling reaction between aryl halides phenylboronic acid assess catalytic abilities complexes. All prepared exhibited considerable activity. However, 4 (Acetonitrile-N2,N6-bis(2-tert-butylphenyl)pyridine-2,6-dicarboxamidopalladium(II)) 5 (Acetonitrile-N2,N6-bis(2-nitrophenyl)pyridine-2,6-dicarboxamidopalladium(II)) provided almost 100% conversion nearly yield 4-bromotoluene acid. these active catalysed sterically hindered deactivated substrates (1-Bromo-4-izobutylbenzene 2-bromo-6-methoxynaphthalene) acid, complete yields up achieved short time 2-bromo-6-methoxynaphthalene.

Language: Английский

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